Sodium borohydride → 4-Cyclopentylbutan-1-ol

HRID 1071173Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1071173
[CH:1]1([CH2:6][CH2:7][CH2:8][CH:9]=[O:10])[CH2:5][CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+]>C(O)C>[CH:1]1([CH2:6][CH2:7][CH2:8][CH2:9][OH:10])[CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 219320564-Cyclopentylbutanal

Produkt 1

HCID 217976434-Cyclopentylbutan-1-olAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

4-Cyclopentyl-butyraldehyde (4.9 g, 35 mmol) was taken up in ethanol (100 mL) and treated slowly with sodium borohydride (1.72 g, 4.54 mmol). The reaction was stirred for three days and quenched with water (10 mL). The reaction was diluted with dichloromethane (200 mL) and washed with water (2×100 mL). The organic phase was dried (MgSO4), filtered, and concentrated to yield an oil. The product was passed through a pad of silica to yield 4-cyclopentyl-butan-1-ol as a colorless oil (3.12 g, 63%).

Aufarbeitung

  1. customquenched with water (10 mL)
  2. additionThe reaction was diluted with dichloromethane (200 mL)
  3. washwashed with water (2×100 mL)
  4. dry with materialThe organic phase was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto yield an oil

Quellen und Nachweise

ORD-Eintrag
ord-1300ab512c8a4751bb1502d043ef4969
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06903218B2

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