Sodium borohydride → Methyl 5-(3-(3-hydroxybutyl)phenyl)isoxazole-3-carboxylate

HRID 1375656Notes

Reaction equation

HRID 1375656 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][CH2:17][C:18](=[O:20])[CH3:19])[CH:11]=2)[O:7][N:6]=1)=[O:4].[BH4-].[Na+]>CO>[OH:20][CH:18]([CH3:19])[CH2:17][CH2:16][C:12]1[CH:11]=[C:10]([C:8]2[O:7][N:6]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:9]=2)[CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 695080965-(3-(3-Oxo-butyl)-phenyl)-isoxazole-3-carboxylic Acid Methyl Ester

Product 1

HCID 69507922Methyl 5-(3-(3-hydroxybutyl)phenyl)isoxazole-3-carboxylateYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 5-(3-(3-Oxo-butyl)-phenyl)-isoxazole-3-carboxylic acid methyl ester (860 mg, 3.15 mmol) in methanol (15 mL)at room temperature was added NaBH4 (178 mg, 4.7 mmol) with stirring. After 30 min, the reaction mixture was partitioned between ethyl acetate and 3N HCl. The organic layer was washed with brine, dried over Na2SO4, filtered, evaporated in vacuo to provide the titled compound as a light brown oil (850 mg, 99% yield).

Workup

  1. customthe reaction mixture was partitioned between ethyl acetate and 3N HCl
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-ee17a314a7444791a170515a9f13affd
Source dataset
uspto-grants-2007_01
Patent number
US07169797B2

Reaction notes

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