Sodium borohydride → (1-Phenylcyclopentyl)methanol

HRID 1409552

Reaktionsgleichung

Reaktionsgleichung von HRID 1409552
[BH4-].[Na+].[C:3]1([C:9]2([CH:14]=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>CO>[C:3]1([C:9]2([CH2:14][OH:15])[CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 110951241-Phenylcyclopentane-1-carbaldehyde

Produkt 1

HCID 123544(1-Phenylcyclopentyl)methanolAusbeute 79,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

NaBH4 (3.2 g, 86.2 mmol) was added portion wise to a cooled (ice bath) solution of 1-phenyl-cyclopentanecarbaldehyde (7.5 g, 43.1 mmol) in methanol (100 ml) and then stirred for 16 h at RT. After completion of the reaction, it was quenched with saturated ammonium chloride solution and the methanol under reduced pressure. The mixture was diluted with water, extracted with EtOAc, washed with water, brine, dried (Na2SO4) and evaporated to dryness under reduced pressure. Chromatography (15% EtOAc in hexanes) provided (1-phenyl-cyclopentyl)-methanol as a white solid (6 g, 79.8%).

Aufarbeitung

  1. customAfter completion of the reaction, it
  2. customwas quenched with saturated ammonium chloride solution
  3. additionThe mixture was diluted with water
  4. extractionextracted with EtOAc
  5. washwashed with water, brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated to dryness under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-091ce8b74e79417386d1143d35765396
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921388B2

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