Water → HCID 59299392, compound

Participants

Reaction Conditions

Reaction Steps

Charge a flask with 1-trimethylsilanyl-pyrrolidin-2-one (5.0 g, 32 mmol), dissolve in THF (150 mL) and cool to −78° C. under nitrogen. Add LDA (2M, 19 mL, 38 mmol) and stir at −78° C. for 10 minutes. Add 2,4-dichloro-1-chloromethyl-benzene (8.1 g, 41 mmol) and warm to room temperature. Pour into water after 2 hours and extract with methylene chloride. Dry over sodium sulfate, filter and concentrate. Purify the residue over silica gel (1:1 hexanes:ethylacetate to 100% ethyl acetate) to afford 5.2 g (67%) of the title compound as a white solid. 1H NMR (CDCl3) δ 7.38 (d, 1H), 7.23 (d, 1H), 7.18 (dd, 1H), 6.01 (bs, 1H), 3.31 (m, 3H), 2.75 (m, 2H), 2.13 (m, 1H), 1.84 (m, 1H).

Provenance & Evidence