Boron trifluoride etherate → HCID 68725689, compound

Participants

Reaction Steps

At −20° C., a solution of ethyl 9-hydroxy-7-methylspiro[4.5]dec-7-ene-6-carboxylate (1.5 g, 6.3 mmol, cis/trans 34:66, prepared as described in example 16) in dichloromethane was treated with successively with triethylsilane (3.66 g, 31.5 mmol) and with BF3.OEt2 (1.34 g, 9.4 mmol). The resulting solution was stirred for 45 min., poured into an ice-cold 2M aqueous NaOH solution (50 ml), and extracted twice with MTBE (40 ml). The organic phases were washed with water (40 ml), with a saturated aqueous solution of NaCl (40 ml), dried (MgSO4) and concentrated. FC (100 g SiO2, hexane/MTBE 25:1) of the crude product (1.28 g) gave ethyl 7-methylspiro[4.5]dec-7-ene-6-carboxylate (0.98 g, 70%).

Provenance & Evidence