Sodium Methoxide → HCID 21825583, compound

Participants

Reaction Steps

Sodium methoxide in methanol (60 mg of sodium in 30 ml of methanol) was added to 1.0 g of 9 and the resulting solution was stirred at room temperature for 4 hr. After neutralization with Amberlite IRC 50, the solution was filtered, and the filtrate was evaporated to dryness. Methanol and silica gel (2.5 g) were added to the syrup, and the mixture was evaporated to dryness. The silica gel mixture was added to a dry-packed silica gel column (1 × 18 cm) and the column was eluted with chloroform (0.1 liter), ethylacetate-chloroform (1:1, 0.1 liter) and ethyl acetate (0.4 liter); 20 ml fractions were collected. Fractions 14-28 provided 0.61 g (91%) of 11 as a syrup: nmr (DMSO-d6) δ 5.95 (d, 1, J1',2' 4.0 Hz, 1'--H), 8.32 (s, 1, 5--H).

Provenance & Evidence