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

HRID 278472노트

반응식

HRID 278472 반응식
[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]

참가 물질

5

반응물 3

HCID 962Water2회HCID 4311764Sodium borohydrideHCID 18370780Methyl 4-(1-naphthyl)-2-oxobutyrate

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-11e47850db2e47e1898dcaaafb442f12
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06359145B1

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