Water → HCID 18989566, compound

HRID 2395703Notes

Reaction equation

HRID 2395703 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([C:14]1[N:15]=[C:16]([CH2:20][C:21](OCC)=[O:22])[O:17][C:18]=1[CH3:19])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O>C(OCC)C>[CH2:7]([C:14]1[N:15]=[C:16]([CH2:20][CH2:21][OH:22])[O:17][C:18]=1[CH3:19])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 18989574HCID 18989574, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18989566HCID 18989566, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of lithium aluminum hydride (LiAlH4) (0.7 g) in ethyl ether (40 ml), a solution of ethyl 2-(4-benzyl-5-methyl-2-oxazolyl)acetate (4.76 g) in ethyl ether (60 ml) was added dropwise under ice cooling conditions, followed by stirring for 1 hour. After water (5 ml) was added dropwise to the reaction mixture, the insoluble substances were filtered off, and the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel chromatography. From the fraction eluted with chloroform-ethyl acetate (2:1, v/v), 2-(4-benzyl-5-methyl-2-oxazolyl)ethanol (3.0 g, 75%) was obtained as an oily substance.

Workup

  1. filtrationthe insoluble substances were filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. washFrom the fraction eluted with chloroform-ethyl acetate (2:1

Sources & evidence

ORD record
ord-71482250bde5486db45ff169e0929d90
Source dataset
uspto-grants-1996_02
Patent number
US05489602

Reaction notes

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