Imidazole → 1-Tert-butyldimethylsilyloxy-2-hydroxy-2-(4-tert-butylphenyl)ethane

HRID 1751861Notes

Reaction equation

HRID 1751861 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([OH:14])[CH2:12][OH:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].N1C=CN=C1.[Si:20](Cl)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]>CN(C=O)C>[Si:20]([O:13][CH2:12][CH:11]([OH:14])[C:8]1[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:10][CH:9]=1)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 190777511-(4-Tert-butylphenyl)ethane-1,2-diol

Product 1

HCID 596786511-Tert-butyldimethylsilyloxy-2-hydroxy-2-(4-tert-butylphenyl)ethane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(4-tert-butylphenyl)ethane 1,2 diol (0.5 g, 2.57 mmol) is dissolved in DMF in a 25 ml round bottom flask and to this were added imidazole (0.210 g, 3.09 mmol) and tert-butyldimethylsilyl chloride (0.46 g, 3.09 mmol). The mixture is stirred for 6 hours after which it is extracted in dichloromethane and the organic layer washed with water and dried. Purification by flash chromatography (silica gel; ethyl acetate/hexanes) affords the above mentioned product.

Workup

  1. extractionis extracted in dichloromethane
  2. washthe organic layer washed with water
  3. customdried
  4. customPurification by flash chromatography (silica gel; ethyl acetate/hexanes)
  5. customaffords the

Sources & evidence

ORD record
ord-f208cb0059554647bdc357d6496b6401
Source dataset
uspto-grants-2015_10
Patent number
US09161997B2

Reaction notes

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