Acetic Anhydride → HCID 68724588, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-hydroxy-1-(7-methylenespiro[4.5]dec-8-en-6-yl)butan-1-one (0.65 mg, 2.77 mmol, 3:1 diastereomeric mixture), acetic anhydride (0.55 ml, 5.8 mmol) and sodium acetate (0.25 g, 3.0 mmol) was stirred at 80° C. for 7 h, treated with sodium acetate (0.1 g, 1.2 mmol), stirred at 80° C. for 7 h, cooled to 0° C., poured into cold saturated aqueous NaHCO3 (20 ml), and extracted three times with MTBE (10 ml). The combined organic phases were washed with a saturated aqueous solution of NaCl, dried (MgSO4), and concentrated. FC (30 g SiO2, hexane/MTBE 40:1) of the crude product (0.49 g) gave (E)-1-(7-methylenespiro[4.5]dec-8-en-6-yl)but-2-en-1-one (0.34 g, 57%). Boiling point: 100° C. (0.07 mbar).

Provenance & Evidence