Water → (4-((Tert-butyldimethylsilyl)oxy)phenyl)methanol

HRID 1794057Notes

Reaction equation

HRID 1794057 reaction equation
[Si:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[BH4-].[Na+].O>CO>[Si:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][OH:14])=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 108791334-{[tert-Butyl(dimethyl)silyl]oxy}benzaldehyde

Product 1

HCID 10014460(4-((Tert-butyldimethylsilyl)oxy)phenyl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

to a stirred solution of 4-(tert-butydimethylsilyloxy)-benzaldehyde (48.0 g, 203 mmol) in methanol (200 mL) at 0° C. was added sodium borohydride (11.6 g, 305 mmol) and the reaction was stirred at 0° C. for 45 min. Water (200 mL) was added and the methanol was removed under reduced pressure. The mixture was extracted with ether (2×200 mL) and ethyl acetate (2×200 mL). The combined organics were dried (MgSO4), filtered and concentrated under vacuum to give the crude product, which was used without further purification (48 g, quantitative).

Workup

  1. customthe methanol was removed under reduced pressure
  2. extractionThe mixture was extracted with ether (2×200 mL) and ethyl acetate (2×200 mL)
  3. dry with materialThe combined organics were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-4b5c32eb10dd4823a827dd5c21d8260e
Source dataset
uspto-grants-2006_04
Patent number
US07022707B2

Reaction notes

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