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

HRID 1953382Notes

Reaction equation

HRID 1953382 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].C(O)C.[BH4-].[Na+].[NH4+].[Cl-]>O>[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

6

Reactant 4

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 108791334-{[tert-Butyl(dimethyl)silyl]oxy}benzaldehyde

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a dry 250 ml round bottom flask was added 2.5 mg of 4, to which was added 100 ml of ethanol. NaBH4 (794 mg) was slowly added thereto and the reaction stirred for 30 minutes. NH4Cl (sat'd solution) was carefully added to the reaction to quench excess NaBH4, and the reaction then diluted with 125 ml water. The mixture was extracted with ether and the organic layers combined and washed with brine. The organic layers were again collected and the solvent removed in vacuo to yield the product 6.

Workup

  1. customto quench excess NaBH4
  2. customthe reaction
  3. extractionThe mixture was extracted with ether
  4. washwashed with brine
  5. customThe organic layers were again collected
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-ff53ca7feddc419aa09c2e5ec4cd0296
Source dataset
uspto-grants-2000_09
Patent number
US06117845

Reaction notes

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