Boron trifluoride etherate → HCID 68724110, compound

Participants

Reaction Steps

At −30° C., a solution of crude trans-methyl 9-hydroxy-7-methylspiro[4.5]dec-7-ene-6-carboxylate (1.1 g, 4.9 mmol, prepared as described in the Example 23) in dichloromethane (10 ml) was treated with triethylsilane (4.0 ml, 24.5 mmol) and with BF3.OEt2 (0.92 ml, 7.4 mmol). The resulting mixture was stirred for 45 min. while allowing the temperature to reach 0° C., poured into cold 2N aqueous NaOH (50 ml), and extracted twice with MTBE (25 ml). The combined organic phases were washed with water (25 ml), with a saturated aqueous solution of NaCl (25 ml), dried (MgSO4), and concentrated. FC (55 g SiO2, hexane/MTBE 40:1) of the crude product (1 g) gave methyl 7-methylspiro[4.5]dec-7-ene-6-carboxylate (0.92 g, 90%). Boiling point: 98° C. (0.07 mbar).

Provenance & Evidence