HCID 68454232, compound → HCID 68452155, compound

Participants

Reaction Steps

To a solution of rac-(1aS,5aR)-2-ethyl-1,1-dimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid (5.9 g, 25.0 mmol) in diethyl ether (420 mL) MeLi (30 mL, 1.6 M solution in diethyl ether) is added at rt. The mixture is stirred at rt for 30 min before another portion of MeLi (6 mL) is added. Stirring is continued at rt for 1 h. The mixture is poured onto ice/water, the organic layer is separated, washed with 1 N aq. NaOH and brine, dried over Na2SO4, and filtered. The solvent is removed in vacuo and the crude product is purified by CC on silica gel eluting with hexane:EA 9:1 to give rac-1-((1aS,5aR)-2-ethyl-1,1-dimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-ethanone (3.7 g) as a pale yellow oil; LC-MS: tR=1.07 min, [M+1]+=235.31, 1H NMR (CDCl3): δ 2.98 (dd, J=5.9, 18.8 HZ, 1H), 2.83-2.70 (m, 3H), 2.40 (s, 3H), 1.94-1.87 (m, 2H), 1.27 (t, J=7.6 Hz, 3H), 1.12 (s, 3H), 0.71 (s, 3H).

Provenance & Evidence