Lithium borohydride → [5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-methanol

HRID 1183266Notes

Reaction equation

HRID 1183266 reaction equation
C[O:2][C:3]([C:5]1[C:6]([CH3:17])=[N:7][O:8][C:9]=1[C:10]1[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][CH:11]=1)=O.[BH4-].[Li+]>CCO>[Br:16][C:13]1[CH:12]=[CH:11][C:10]([C:9]2[O:8][N:7]=[C:6]([CH3:17])[C:5]=2[CH2:3][OH:2])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 56604575Methyl 5-(4-bromophenyl)-3-methylisoxazole-4-carboxylate

Product 1

HCID 58218538[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

5-(4-Bromo-phenyl)-3-methyl-isoxazole-4-carboxylic acid methyl ester (5 g, 16.8 mmol) and lithium borohydride (1.85 g, 84.1 mmol) were combined in EtOH and stirred at 60° C. After aqueous workup, the crude material was purified by silica gel chromatography to give the title compound.

Workup

  1. customAfter aqueous workup, the crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-f1f87bf6c65f4fedbc6ff09c4e4ae778
Source dataset
uspto-grants-2014_03
Patent number
US08664220B2

Reaction notes

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