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

HRID 1278804Notes

Reaction equation

HRID 1278804 reaction equation
[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]

Participants

4

Reactant 3

HCID 702Ethanol2×HCID 9032Potassium CyanideHCID 86584130HCID 86584130, compound

Product 1

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

Procedure

To a suspension of potassium cyanide (0.176 g, 2.70 mmole) in absolute ethanol (43mL) 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); δ 7.38-7.16 (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.

Workup

  1. customwas removed
  2. additionthe reside was diluted with water
  3. extractionThe organics were extracted with ether
  4. additionsilica gel (60 mL) was added
  5. customthe solvent was removed
  6. customchromatographed

Sources & evidence

ORD record
ord-baad3cb97b9e4edeb5afe1aea66cb6cb
Source dataset
uspto-grants-2002_09
Patent number
US06444670B2

Reaction notes

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