Acetaldehyde → HCID 13833724, compound

Participants

Reaction Steps

To a solution of 5-bromo-3,3-dimethyl-2,3-dihydro-benzofuran (example 1f) (3.50 g, 15.4 mmol) in dry THF (20 mL) at −78° C., under argon, was added dropwise n-BuLi (1.6 M in hexane, 23.1 mmol, 14.4 mL). The mixture was stirred for 2 hours then acetaldehyde (0.95 mL) was added and the mixture was slowly warmed up to room temperature and stirred overnight at room temperature. 1N HCl was added and the solution extracted with ethyl acetate and the organic extract was dried (MgSO4), filtered and evaporated to give 3.3 g of 1-(3,3-dimethyl-2,3-dihydro-benzofuran5-yl)-ethanol. 1H NMR (300 MHz; CDCl3): δ 1.35 (s, 6H), 1.49 (d, J=6.5 Hz, 3H), 4.24 (s, 2H), 4.86 (q, J=6.5 Hz, 1H), 6.75 (d, J=8.2 Hz, 3H), 7.10–7.15 (m, 2H).

Provenance & Evidence