Ethyl isobutyrate → Ethyl 2,2-dimethylnon-8-enoate

Participants

Reaction Steps

A solution of n-BuLi 2.5 M in hexanes (3.79 mL, 9.48 mmol) was added at −78° C. under nitrogen to a solution of diisopropylamine (1.33 mL, 9.46 mmol) in dry THF (10 mL). After 15 min, a solution of ethylisobutyrate (1.0 g, 8.61 mmol) in dry THF (5.0 mL) was slowly added. After 30 min at −78° C., a solution of 7-bromohept-1-ene (1.68 g, 9.47 mmol) in HMPA (2.0 mL) was added drop wise and the reaction mixture was allowed to warm up to room temperature. After 16 h, the reaction mixture was quenched with diluted HCl, extracted with AcOEt, washed with brine, dried (MgSO4), filtered and concentrated. Purification by flash chromatography (DCM/heptane, 2:8) afforded 800 mg (44%) of the title product (51) as a colorless oil. TLC (DCM/hexanes 1/1): Rf=0.7.

Provenance & Evidence