Sodium borohydride → 4-Cyclopentylbutan-1-ol

HRID 1004645Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1004645
[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-1612288e8b024818bf4af09b0642a0cc
Quelldatensatz
uspto-grants-2000_04
Patentnummer
US06051586

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