Methanol → HCID 12920419, compound

Participants

Reaction Steps

To a stirred solution of 7.80 g (0.069 mol) of α-methyl-δ-valerolactone in 5 mL of dry methanol was added 6 mL of conc. sulfuric acid. After 20 min the mixture was neutralized with 200 mL of cold satd. sodium bicabonate solution and extracted with 4×20 mL of cold dichloromethane. The cold extracts were dried (MgSO4) and the solution immediately added to a stirring suspension of 53.99 g (2.7 equivalent) of pulverized pyridinium chlorochromate and 1.85 g (0.0226 mol) of sodium acetate in 80 mL of dry dichloromethane. After 30 min 3 g of silica gel was added and the slurry poured onto a 150 g silica gel column. Elution with ether, concentration of the eluate, solution of the residue in 20 mL of dichloromethane and washing of the solution with 3×30 mL of 1 M HCl and 3×30 mL of satd. aqueous sodium bicarbonate, concentration and distillation gave 1.6-4.0 g (16-40%) of the title product, bp 90°-115° C. (0.6 mm); NMR δ9.75 (t, 1H).

Provenance & Evidence