Sodium borohydride → 2-Chloro-1-(6-fluoro-1-benzopyran-2-yl)-ethanol

HRID 875255Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 875255
[Cl:1][CH2:2][C:3]([CH:5]1[CH:10]=[CH:9][C:8]2[CH:11]=[C:12]([F:15])[CH:13]=[CH:14][C:7]=2[O:6]1)=[O:4].[BH4-].[Na+]>C(O)C.O.ClCCl>[Cl:1][CH2:2][CH:3]([CH:5]1[CH:10]=[CH:9][C:8]2[CH:11]=[C:12]([F:15])[CH:13]=[CH:14][C:7]=2[O:6]1)[OH:4]

Komponenten

6

Edukt 2

HCID 4311764Sodium borohydrideHCID 866579942-Chloro-1-(6-fluoro-1-benzopyran-2-yl)-ethanone

Produkt 1

HCID 672125072-Chloro-1-(6-fluoro-1-benzopyran-2-yl)-ethanolAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A stirred solution of 2-Chloro-1-(6-fluoro-1-benzopyran-2-yl)-ethanone (0.33 g, 1.28 mmol, 88.4% A) in ethanol (2.5 ml) was cooled to 0° C. under nitrogen. NaBH4 (60.1 mg, 1.59 mmol) was added to the solution and the reaction mixture stirred for 2 hours. After checking by GPC that the starting product had disappeared, the mixture was diluted with demineralized water (7 ml) and dichloromethane (7 ml) and the phases separated. The organic layer was dried over anhydrous sodium sulphate, filtered and concentrated under vacuum to give crude 2-Chloro-1-(6-fluoro-1-benzopyran-2-yl)-ethanol as a mixture of diastereoisomers 54:46 (0.30 g, 70% yield, 67.9% A).

Aufarbeitung

  1. customthe phases separated
  2. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-be09a0a66b9d45849aaa9811caf8eb00
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08981127B2

Notizen zur Reaktion

Wird geladen…