Water → Methyl 2-hydroxy-4-(1-naphthyl)butyrate

HRID 278472Notes

Reaction equation

HRID 278472 reaction equation
[BH4-].[Na+].[C:3]1([CH2:13][CH2:14][C:15](=[O:20])[C:16]([O:18][CH3:19])=[O:17])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.O>C1COCC1>[OH:20][CH:15]([CH2:14][CH2:13][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1)[C:16]([O:18][CH3:19])=[O:17]

Participants

5

Reactant 3

HCID 962Water2×HCID 4311764Sodium borohydrideHCID 18370780Methyl 4-(1-naphthyl)-2-oxobutyrate

Product 1

HCID 22628549Methyl 2-hydroxy-4-(1-naphthyl)butyrateYield 33.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

NaBH4 (22 mg) was added portionwise to an ice cooled solution of methyl 4-(1-naphthyl)-2-oxobutyrate (obtained in Preparation 12) (252.5 mg) in THF(5 ml)-H2O (1 ml). After the addition was completed, the reaction mixture was stirred at ice-bath temperature for 30 minutes. Water (4 ml) was added, and the resulting mixture was stirred for several minutes and then extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by silica gel (5 g) column chromatography eluting with hexane/ethyl acetate (10:1) to give methyl 2-hydroxy-4-(1-naphthyl)butyrate (84.4 mg) as a colorless oil.

Workup

  1. additionAfter the addition
  2. stirringthe resulting mixture was stirred for several minutes
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel (5 g) column chromatography
  8. washeluting with hexane/ethyl acetate (10:1)

Sources & evidence

ORD record
ord-11e47850db2e47e1898dcaaafb442f12
Source dataset
uspto-grants-2002_03
Patent number
US06359145B1

Reaction notes

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