Methanol → (s)-3,4-Epoxybutyric acid tetrabutylammonium salt

HRID 1595031Notes

Reaction equation

HRID 1595031 reaction equation
O.C([O:5][C@H:6]([CH2:11]Br)[CH2:7][C:8]([OH:10])=[O:9])(=O)C.CO.[OH-].[CH2:16]([N+:20]([CH2:29][CH2:30][CH2:31][CH3:32])([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:21][CH2:22][CH2:23][CH3:24])[CH2:17][CH2:18][CH3:19]>>[CH2:29]([N+:20]([CH2:16][CH2:17][CH2:18][CH3:19])([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:25][CH2:26][CH2:27][CH3:28])[CH2:30][CH2:31][CH3:32].[O:5]1[CH2:11][C@@H:6]1[CH2:7][C:8]([O-:10])=[O:9]

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 2723671Tetrabutylammonium HydroxideHCID 2733880(3S)-3-acetyloxy-4-bromobutanoic acid

Product 1

HCID 9841041(s)-3,4-Epoxybutyric acid tetrabutylammonium salt

Procedure

A solution of distilled water (10 ml), (S)-3-acetoxy-4-bromobutyric acid (0.9 g, 0.004 mol) and 1.0M methanol (12 ml, 0.012 mol) in tetrabutylammonium hydroxide was charged to 100 ml flask equipped with a thermometer, pH meter and agitator, and stirred at 0˜5° C. for 2 hours to give (S)-3,4-epoxybutyric acid tetrabutylammonium salt. It was confirmed by a NMR analysis that more than 99% (S)-3,4-epoxybutyric acid tetrabutylammonium salt was converted.

Workup

  1. customequipped with a thermometer

Sources & evidence

ORD record
ord-b8c81dee56b64516ab3cf1616f1da118
Source dataset
uspto-grants-2001_09
Patent number
US06284902B1

Reaction notes

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