Ethanol → Ethyl 2-(2-oxocyclopentyl)acetate

反応式

[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[CH2:7][C:8]([OH:10])=[O:9].OS(O)(=O)=O.[CH2:16](O)[CH3:17]>>[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[CH2:7][C:8]([O:10][CH2:16][CH3:17])=[O:9]

参加物

反応物 3

HCID 702Ethanol

HCID 1118Sulfuric Acid

HCID 35699832-(2-oxocyclopentyl)acetic Acid

生成物 1

HCID 2723663Ethyl 2-(2-oxocyclopentyl)acetate

実験手順

To a solution of 2-(2-oxocyclopentyl)acetic acid (23.6 g, 166 mmol) in absolute ethanol (400 mL) was added H2SO4 (16.28 g, 166 mmol). The resultant solution was heated under reflux overnight. The reaction mixture was concentrated and the liquid residue was added into ice-water (200 mL). The aqueous mixture was extracted with DCM (3×200 mL). The combined organic layers were washed with H2O (300 mL), brine (300 mL), dried over Na2SO4, decanted, concentrated and dried under vacuum to afford the title compound as a light yellow liquid (27.2 g). LCMS m/z=171.3 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 1.19 (t, J=7.14 Hz, 3H), 1.50-1.62 (m, 1H), 1.65-1.80 (m, 1H), 1.92-2.02 (m, 1H), 2.12 (dd, J=16.7, 8.86 Hz, 1H), 2.19-2.29 (m, 2H), 2.30-2.44 (m, 2H), 2.65 (dd, J=15.12, 2.6 Hz, 1H), 4.07 (q, J=7.14 Hz, 2H).