Acetaldehyde → HCID 68725455, compound

Participants

Reaction Steps

At −70° C. under N2, a solution of diisopropylamine (0.91 ml, 6.5 mmol) in anhydrous THF (10 ml) was treated dropwise with a solution of 1.6M n-BuLi in hexane (4 ml, 6.5 mmol). The resulting solution was stirred for 20 min., and treated dropwise with a solution of a 3:90:7 mixture of 1-(7-methylspiro[4.5]deca-7,9-dien-6-yl)ethanone, 1-(7-methylenespiro[4.5]dec-8-en-6-yl)ethanone, and 1-(7-methylspiro[4.5]deca-6,8-dien-6-yl)ethanone (0.94 g, 4.98 mmol) in anhydrous THF (4 ml). The resulting solution was stirred for 45 min. at −50° C., treated with a solution of acetaldehyde (1.2 ml, 20 mmol) in anhydrous THF (4 ml). The resulting solution was stirred at −40° C. for 1 h, poured into a mixture of ice and 2N HCl, and extracted three times with MTBE (25 ml). The combined organic phases washed with a saturated aqueous solution of NaCl, dried (MgSO4), and concentrated. FC (40 g SiO2, hexane/MTBE 10:1) of the crude product (1.3 g) gave 3-hydroxy-1-(7-methylenespiro[4.5]dec-8-en-6-yl)butan-1-one (0.788 g, 68%, 3:1 diast. mixture)

Provenance & Evidence