Ethanethiol → HCID 60128070, compound

Participants

Reaction Conditions

Reaction Steps

A solution of methyl (2S)-2-[(1S)-5methoxy-2,3-dihydro-1H-inden-1yl]propanoate (Example 11) (5.70 g, 0.024 mol) in CH2Cl2 (70 mL), under argon, was cooled to 0-5° C. and AlCl3 (16.22 g, 0.122 mol) was added portion-wise while maintaining the temperature below 10° C. To this mixture was added EtSH (9.0 mL, 0.122 mol) and the resulting mixture was stirred at 0-5° C. for 4 h. The reaction mixture was then slowly poured into vigorously stirred ice-water (200 mL) and the aqueous layer was extracted with CH2Cl2. The combined organic layers were washed with water, brine, dried (Na2SO4), filtered, and concentrated to dryness under vacuum. The resulting crude product was purified by silica gel flash chromatography (gradient of 10-40% ethyl acetate/hexanes) to give 4:2 g (80%) of the title compound. 1H NMR (400 MHz, CDCl3): δ 6.93 (d, 1H), 6.70 (s, 1H), 6.63 (dd, 1H), 3.72 (s, 3H), 3.50 (q, 1H), 2.83 (m, 3H), 2.19 (m, 1H), 1.90 (m, 1H), 1.08 (d, 3H); LC-MS: RT=8.60 min, (M+H)+ 220.

Provenance & Evidence