Methanol → HCID 12920419, compound

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).

1. extractionsodium bicabonate solution and extracted with 4×20 mL of cold dichloromethane
2. dry with materialThe cold extracts were dried (MgSO4)
3. additionAfter 30 min 3 g of silica gel was added
4. additionthe slurry poured onto a 150 g silica gel column
5. washElution with ether, concentration of the eluate, solution of the residue in 20 mL of dichloromethane
6. washwashing of the solution with 3×30 mL of 1 M HCl and 3×30 mL of satd
7. concentrationaqueous sodium bicarbonate, concentration and distillation

ORD record

ord-edcbc01485f34fdca203418f08f3e473

Source dataset

uspto-grants-1990_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04897477