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

HRID 1069220Notes

Reaction equation

HRID 1069220 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 (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.

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-3d88e58d1b294bcaad896ba060dec1ee
Source dataset
uspto-grants-2001_06
Patent number
US06251936B1

Reaction notes

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