Sodium borohydride → 5-(tert-Butyl)-2-(hydroxymethyl)phenol

HRID 1765815Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1765815
[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH:19]=[O:20])=[C:9]([O:11]S(C(F)(F)F)(=O)=O)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(C1C=CC(C=O)=C(O)C=1)(C)(C)C.[BH4-].[Na+]>CO.O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH2:19][OH:20])=[C:9]([OH:11])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 3

HCID 4311764Sodium borohydrideHCID 137652724-tert-Butyl-2-hydroxybenzaldehydeHCID 57424249Trifluoro-methanesulfonic acid 5-tert-butyl-2-formyl-phenyl ester2×

Produkt 1

HCID 196902415-(tert-Butyl)-2-(hydroxymethyl)phenol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A stirred, cooled (ice-bath) solution of a 1:1 mixture of trifluoro-methanesulfonic acid 5-tert-butyl-2-formyl-phenyl ester and 4-tert-butyl-2-hydroxy-benzaldehyde (Intermediate 105, 0.47 g) in methanol (8 mL) was treated with sodium borohydride (0.1 g, 2.64 mmol). After 1 h, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic phase was washed with water and brine, dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to a residue that was subjected to flash column chromatography on silica gel (230–400 mesh) to afford the title product (0.3 g).

Aufarbeitung

  1. temperatureA stirred, cooled
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo to a residue that

Quellen und Nachweise

ORD-Eintrag
ord-b69e4c0de991430db3f0d33b68181095
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07226951B2

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