Ethanol → (S)-Ethyl 2-hydroxy-4-phenylbutanoate

反応式

[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]

参加物

反応物 3

HCID 702Ethanol2 回

HCID 9032Potassium Cyanide

HCID 86584130HCID 86584130、化合物

生成物 1

HCID 10987483(S)-Ethyl 2-hydroxy-4-phenylbutanoate収率 74%

実験手順

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.