Sodium borohydride → HCID 69527632, Verbindung

HRID 1828807Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1828807
[O:1]([CH2:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=[O:25])=[CH:22][C:21]=1[Cl:28])[Si:2]([C:15]([CH3:18])([CH3:17])[CH3:16])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[BH4-].[Na+]>C(O)C>[O:1]([CH2:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][OH:25])=[CH:22][C:21]=1[Cl:28])[Si:2]([C:15]([CH3:17])([CH3:18])[CH3:16])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 22058586HCID 22058586, Verbindung

Produkt 1

HCID 69527632HCID 69527632, VerbindungAusbeute 94,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a suspension of 4-((tert-butyldiphenylsiloxy)methyl)-3-chlorobenzaldehyde (3.24 g) in ethanol (32 ml) was added sodium borohydride (149 mg) under ice-cooling and the mixture was stirred at room temperature for 3 hr. The reaction mixture was concentrated to about half amount. Water was added and the resulting product was extracted twice with diisopropyl ether. The organic layers were combined, washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1) to give 4-((tert-butyldiphenylsiloxy)methyl)-3-chlorobenzyl alcohol (3.08 g) as a colorless oil.

Aufarbeitung

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated to about half amount
  3. additionWater was added
  4. extractionthe resulting product was extracted twice with diisopropyl ether
  5. washwashed successively with saturated aqueous sodium hydrogencarbonate solution and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated
  8. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1)

Quellen und Nachweise

ORD-Eintrag
ord-27354e00d3b34f24ae97da49e0cbe085
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07060721B1

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