乙醇 → (S)-4-苯基-2-羟基丁酸乙酯

反应方程式

[C-]#N.[K+].[N+](C1C=CC(C([C@H:13]([CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:14]([O:16][CH2:17][CH3:18])=[O:15])=O)=CC=1)([O-])=O.C([OH:31])C>>[OH:31][C@@H:13]([CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:14]([O:16][CH2:17][CH3:18])=[O:15]

参与物

反应物 3

HCID 702乙醇2 次

HCID 9032氰化钾

HCID 86584130HCID 86584130，化合物

产物 1

HCID 10987483(S)-4-苯基-2-羟基丁酸乙酯收率 74%

实验过程

To a suspension of potassium cyanide (0. 176 g, 2.70 mmole) in absolute ethanol (43 mL) was added a solution of (S)-2-[4-nitrobenzoyl]-4-phenylbutyric acid, ethyl ester (3.86 g, 10.8 mmole) in absolute ethanol (38 mL) dropwise over a period of 0.5 hours. After stirring 2.25 hours the solvent was removed and the reside was diluted with water and acidified with dilute hydrochloric acid. The organics were extracted with ether. The extracts were combined, silica gel (60 mL) was added and the solvent was removed. The adsorbate was flash chromatographed, eluent (gradient 90/10-80/20 petroleum ether/ethyl acetate) and the solvents were chased with benzene to give the title compound as a yellow oil (1.67 g, 74%): NMR (CDCl3); δ7.38-7.16 (m, 5H), 4.30-4.10(m, 3H), 2.9-2.6 (m, 3H,), 2.2-1.9(m, 2H), 1.15(t, 4 Hz, 3H); [a]25D +178.23 at 10.98 mg/mL CHCl3.