Diketene → HCID 19894041, compound

Participants

Reaction Steps

To a mixture of 7-(3-methylisoxazol-5-yl)heptan-1-ol (1.97 g, 0.01 mol) and anhydrous sodium acetate (0.080 g) in benzene (20mL) was added a solution of diketene (1.84 g, 0.022 mol) in benzene (6 mL) dropwise. The mixture was refluxed for 12 h. After the removal of benzene under reduced pressure, the crude product was purified by elution from a silica gel column using dichloromethane-hexane (9:1 v/v) as eluant to give 5-(7-acetoacetoxyhept-1-yl)-3-methylisoxazole (21) (70%) as a yellow oil. IR (neat) 1740 (CO2), 1718 (CO)cm-1 ; NMR (CDCl3) 1.12-1.95 (m, 10H, (CH2)5), 2.35 (S, 6H, Me-Het, CO-Me), 2.70 (t, J=9 Hz, 2H, CH2 --Het), 3.49 (S, 2H, CO--CH2 --COMe), 4.14 (t, J=6 Hz, 2H, O--CH2), 5.80 (S, 1H, H-Het). Analysis found: C, 64.11; H, 8.31; N, 4.72. Required: C, 64.02; H, 8.24; N, 5.00 (C15H23NO4). ##STR8##

Provenance & Evidence