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

HRID 278472

Reaktionsgleichung

Reaktionsgleichung von HRID 278472
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 22628549Methyl 2-hydroxy-4-(1-naphthyl)butyrateAusbeute 33,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-11e47850db2e47e1898dcaaafb442f12
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06359145B1

Verknüpfte Notizen

Wird geladen…