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14.7.2.2.1.1 Method 1: From 4-Hydroxy-3,4-dihydro-1H-2-benzothiopyrans

DOI: 10.1055/sos-SD-014-00832

Rudorf, W.-D.Science of Synthesis, (200314749.

Reduction of a ketone is often used to introduce the hydroxy group that is eliminated. Dehydration and dehydrogenation can be carried out in a one-pot reaction subject to the choice of reagents.

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Meeeee 88 8-Meeeeeeeeeeeeeeee Meeee eeee 8-Meeeeee-8,8-eeeeeee-8M-8-eeeeeeeeeeeeeee[‌8‌,‌8‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeeeeeeeeeeeeee Meeeeeeeeee (888):[‌8‌]

MMMMMMM: Meeeeee eeee eeeeeeeeeee eee eeeeeee eeee e eeeeee ee eeeeeee eeeeee eeeeeee eeeeeeee, eee eeeeeeeeeee ee eeeeeeeee eeeeeeeeeeeeeeeee eeee eeeeeee eeeeee eeee eeeeeeee eeeeeeeee eeeee eeeee eeeeee ee eeeeeee eeeeeeeeeee.[‌88‌]

8-Meeeeee-8,8-eeeeeee-8M-8-eeeeeeeeeeeeee (888; 8e, 88eeee) eee eeeeeeeeeeeeeeeeee eeeeeeeeeee (8.8e, 88eeee) eeee eeeeeeee ee eeeeeee MeMM (88eM) eee 88eee. Me eeee eeeeeee eee eeeeeeeeeee, eeeee eeeeeee eeeeeeeee; eeeee: 8.8e (88%); ee 888888°M. Meee eeee eeeeeeeeeeeeee (MeMM eeee e eeeeee Me8M); ee 888888°M.

Meeeeee[8,8-e]eeeeeeeeeeee Meeeeeeeeee (888); Meeeeee Meeeeeeee:[‌8‌]

8M-Meeeeee[8,8-e]eeeeeeeee-8(8M)-eee:

M eeeee ee M8M88 (88e, 8.888eee), Meeeee (88e), eee eee eeeeeee (888eM) eee eeeee eeee eeeee eeeeeeee ee e eeee ee [(8-eeeeeeeeeeeeee)eeeeeeee]eeeeee eeee (88.88e, 8.888eee) ee eeeeeeeee eee eeeeeee (888eM). Mee eeeeee eee eeeeeee ee eeeeee eeee eeeeeeee eeeeeeee eee 88eee, eeee e eeeee ee M8M88 (88e, 8.888eee) ee eee eeeeeee (88eM) eee eeeee. Meeee eeeeeeeee eee ee eeeeeeeeee 88eee, eeeeeee eeeeeeeee eeeee eee eeeee eee eee eeeeeee eeee eeeeeeee eee ee eeeeeeeeee 88eee. Mee eeeeeee eeeeee eee eeeeeeee eee eee eee eeeeeeeee eee eeee eee eeeeeeeee eeee eeeeeee eeeeeee (8×888eM). Mee eeeeeeee eeee eeeeeeee eee eeeeee eeee 8% MeMMM8 (8×888eM) eeeeeeee ee eeeee (888eM). Mee eeee eee eeeee (MeMM8), eeeeeeee, eee eee eeeeeee eee eeeeeee ee eeeee ee eeeee e eeeeee eee eeeee eeeeeeeeee ee eeeeeeee ee 8°M eeeeeeeee. Mee eeeee eee eeeeeeeee ee eeeeeee 88% MeMM (888eM) eee eeeeeeee eeee e eeeee eeeeee ee eeeeeeeee eee eee. Meeee 8e ee 8°M ee eeeeee eee eeeee eeee eeee eeee eeeeee eeeee eeeeeeeeeeee. Mee eeee eee eeeeee eeee eeeeee ee eee eee eeeeeeee eeee eeee eeee eee eee eeee eee eeeeeeee eeee eee eee eee. Me eeeeeee eeeeeeeee, eee MeMM eeee eeee eeee eeeeee eeeeeeee; eeeee: 8.88e (88%); ee 888888°M. Meeeeeeeeee (888°M/8.88Meee) eeeeeeee ee eeeeeeeeeeeeeeeee (88% MeMM) eee ee eeee eeeeee eeeeee; eeeee: 8.88e (88%); ee 888888°M.

8-Meeeeee-8,8-eeeeeee-8M-eeeeeee[8,8-e]eeeeeeeee:

M eeee ee 8M-eeeeeee[8,8-e]eeeeeeeee-8(8M)-eee (8.88e, 8.8eeee) ee eee Me8M (888eM) eee eeeeee eeeee ee e eeeeeee eeeeeeeeee ee MeMeM8 (8.88e, 88.8eeee) ee eee Me8M (888eM). Mee eeeeeee eee eeeeeee eee 88eee, eeee MeMMe (88eM) eee eeeeeeeeee eeeee eeeeeeee ee eeeee (88eM). Mee Me eeeee eeee eeeeeeee eee, eee Me8M eeee eee eeeee (MeMM8), eeeeeeee, eee eeeeeeeeee ee eeeee ee eeee e eeeee eeeeeeeeeee eeeeeee; eeeee: 8.88e (88%); ee 888888°M. Meeeeeeeeeeeeeeee [eeeeeee/eeeeeeeee eeeee (ee 8888°M)] eeeeeeee ee eeeeeeeeeee (888°M/8.88Meee) eee ee eeee 8-eeeeeee-8,8-eeeeeee-8M-eeeeeee[8,8-e]eeeeeeeee; ee 888888°M.

Meeeeee[8,8-e]eeeeeeeeeeee Meeeeeeeeee (888):

M eeee ee eeeeeeeeeeeeeeeeee eeeeeeeeeee (8.88e, 8.88eeee) ee MeMM8 (88eM) eee eeeee ee eee eeeeeee ee e eeeeeee eeee ee 8-eeeeeee-8,8-eeeeeee-8M-eeeeeee[8,8-e]eeeeeeeee (8.88e, 8.88eeee) ee eeeeeeeee MeMM (88eM). Mee eeee eeeeee eeeeeeee-eeeee eeeeeeeeeee. Me eee eeee eee eeeeeeee eee 88eee eeeee eeeeeeee eeeeee ee eee eeee ee eee eeeeeeee eeeee. Mee eeeeeee eee eeee eeeeee eee eee eeeee eeeeeeee (eeeee: 8.88e; ee >888°M) eeee eeeeeee ee eeeeeeeeee. MeMM8 eee eeeeeee ee eeeee eee eee eeeeeeeee eeee eeeeeee eeee eee Me8M (888eM). Mee eeeeeeee-eeeee eeeeeeee eeeee eeeeeeeeeeee eeee eeeeeeeee ee eeeeeeeeee eee eeeee ee eeeee eeee MMM; eeeee: 8.88e (88%); ee 888888°M (eee). Meeeeeee eeeeeeeeeeeeeeeeee (MeMM) eeee eeeee eeeeee eeeeeee; ee 888.8888°M.

Meeeeee[8,8-e]eeeeeeeeeeee Meeeeeeeeee (888); Meeeeee Meeeeeeee:[‌8‌]

8-Meeeeee-8,8-eeeeeee-8M-eeeeeee[8,8-e]eeeeeeeee:

M eeee ee 8M-eeeeeee[8,8-e]eeeeeeeee-8(8M)-eee (8.88e, 8.8eeee) ee eee Me8M (888eM) eee eeeeee eeeee ee e eeeeeee eeeeeeeeee ee MeMeM8 (8.88e, 88eeee) ee eee Me8M (888eM). Mee eeeeeee eee eeeeeee eee 88eee eee eeee MeMMe (88eM) eee eeeee eeeeeeeeee, eeeeeeee ee eeeeeeee ee eeeee (88eM). Mee Me8M eeee eee eeeeeeee ee eeeeee eee eeeeeeeeeeee eeeee, eeeee (MeMM8), eeeeeeee, eee eeee eeeeeeeeee ee eeeeeee ee eeee ee eee eeeee eeeee; eeeee: 8.88e (88%); ee 888888°M. Mee eeeeeeeeeeeeeeeee [eeeeeeeee eeeee (ee 8888°M)] eeeeeeee ee eee eeeeeeeeeeee (88°M/8.88Meee) eee ee eeee 8-eeeeeee-8,8-eeeeeee-8M-eeeeeee[8,8-e]eeeeeeeee; ee 888.8888.8°M.

Meeeeee[8,8-e]eeeeeeeeeeee Meeeeeeeeee (888):

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References


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