Imidazole → 4-(tert-Butyldimethylsiloxy)phenol

HRID 221632

Reaction equation

HRID 221632 reaction equation
C([O:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)(=O)C1C=CC=CC=1.[CH3:17][C:18]([Si:21](Cl)([CH3:23])[CH3:22])([CH3:20])[CH3:19].N1C=CN=C1.[BH4-].[Na+]>C(Cl)Cl.CO>[C:18]([Si:21]([CH3:23])([CH3:22])[O:9][C:10]1[CH:11]=[CH:12][C:13]([OH:16])=[CH:14][CH:15]=1)([CH3:20])([CH3:19])[CH3:17]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 75549p-Hydroxyphenyl benzoateHCID 4311764Sodium borohydride

Product 1

HCID 5973884-(tert-Butyldimethylsiloxy)phenol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

4-Hydroxyphenyl benzoate (9.0 mmol) was dissolved in CH2Cl2 (9 mL/mmol), TBDMS-Cl (1.5 eq., 13.5 mmol) and imidazole (2.0 eq., 18.0 mmol) were added and the mixture was stirred at r.t. overnight. The mixture was diluted with MeOH (4.5 mL/mmol), and NaBH4 (2.5 eq., 22.5 mmol) was added slowly over 5 min (attention: vigorous gas evolution). The mixture was concentrated by removing CH2Cl2 under reduced pressure and the suspension was heated to 65° C. for 15 h.

Workup

  1. additionwas added slowly over 5 min (attention: vigorous gas evolution)
  2. concentrationThe mixture was concentrated
  3. customby removing CH2Cl2 under reduced pressure
  4. temperaturethe suspension was heated to 65° C. for 15 h.

Sources & evidence

ORD record
ord-76d530adac7142d98b992c5740c45a81
Source dataset
uspto-grants-2012_06
Patent number
US08207174B2

Linked notes

Loading…