Sodium borohydride → 6-Bromo-1,2,3,4-tetrahydronaphthalen-1-ol

HRID 63632

Reaktionsgleichung

Reaktionsgleichung von HRID 63632
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2.[BH4-].[Na+]>CCO.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]([OH:12])[CH2:7][CH2:6][CH2:5]2

Komponenten

5

Edukt 2

HCID 4311764Sodium borohydrideHCID 101050696-Bromo-1-tetralone

Produkt 1

HCID 184699326-Bromo-1,2,3,4-tetrahydronaphthalen-1-olAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 6-bromo-1,2,3,4-tetrahydronaphthalen-1-one (2.0 g, 8.9 mmol) in EtOH (20 mL) was added NaBH4 (1.6 g, 42.7 mmol) at rt, and the reaction was stirred for 30 min. The reaction was diluted with water (10 mL) and extracted with EtOAc (3×50 mL). Organics were washed with brine (50 mL), dried (Na2SO4) and concentrated to give 1.9 g (94%) of the title compound as a brown oil. [M+H] calc'd for C10H11BrO2, 227, 229. found 227, 229.

Aufarbeitung

  1. extractionextracted with EtOAc (3×50 mL)
  2. washOrganics were washed with brine (50 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d8692e0a624043d49fcbd98aacc92b89
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447046B2

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