HCID 10597031, compound → HCID 10548794, compound

Participants

Reaction Steps

Potassium t-butoxide (0.195 g, 1.73 mmol) was added to a stirred suspension of methyl triphenylphosphonium bromide (0.618 g, 1.73 mmol) in dry benzene (8 mL), which was maintained under argon at room temperature. After stirring for 30 min, the reaction mixture was cooled to 0° C. and a solution of ketone 3.17 (0.46 g, 1.16 mmol) in dry THF was added rapidly. The reaction mixture was quenched after 30-60 minutes at 0° C. with brine (~10 mL), extracted with EtOAc (3×20 mL), and the combined organic layer was washed with water (1×10 mL) and dried (Na2SO4). The residue obtained after concentration was purified by flash column chromatography over silica gel using hexane:EtOAc (95:5) giving 3.18 as a liquid (0.72g, 71.5%); IR (neat) 1738 (C=O) and 1647 cm-1 ; 1H NMR (CDCl3) δ 0.85(distorted t, 3H, CH3 (CH2)13), 1.20-1.40 (m, 25 H, CH3 (CH2)11CH2CH2OCO, CH3CH2OCO), 1.60 (m, 2 H, CH3 (CH2)11CH2CH2OCO), 2.35 (m, 4 H, OCCH2CH2 (C=CH2)CH2CH2CO), 2.45 (m, 4 H, OCCH2CH2 (C=CH2)CH2CH2CO), 4.00-4.15 (m, 4H, CH3 (CH2)11CH2CH2OCO, CH3CH2O), 4.75 (s, 2 H, =CH2); 13C NMR (CDCl3) δ 14.09, 14.20, 22.66, 25.89, 28.60, 29.23, 29.33, 29.50, 29.56, 29.62, 31.00, 31.03, 31.89, 32.64, 60.35, 64.61, 109.75, 146.37, 173.08, 173.181. Anal. Calcd for C24H44O4 : C, 72.67; H, 11.19. Found: C, 72.63; H, 11.23.

Provenance & Evidence