Imidazole → 4-(4-Methylphenyl)butyl tert-butyldimethylsilyl ether

HRID 1516081Notes

Reaction equation

HRID 1516081 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][OH:12])=[CH:4][CH:3]=1.N1C=CN=C1.[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]>CN(C=O)C>[Si:18]([O:12][CH2:11][CH2:10][CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 1040094-(4-Methylphenyl)butanol

Product 1

HCID 596786264-(4-Methylphenyl)butyl tert-butyldimethylsilyl ether

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(4-Methylphenyl)butanol (0.5 g, 3.04 mmol) is dissolved in 5 ml DMF and to it is added imidazole (310 mg, 4.56 mmol) and tert-butyldimethylsilyl chloride (685 mg, 4.56 mmol). The reaction is stirred for 4 hrs after which it is extracted in ethyl acetate and washed with water to remove all DMF. The organic layer is then dried and concentrated. The crude mixture is then purified by flash chromatography using a mixture of ethyl acetate-hexanes as the eluting medium to afford the above mentioned product.

Workup

  1. extractionis extracted in ethyl acetate
  2. washwashed with water
  3. customto remove all DMF
  4. customThe organic layer is then dried
  5. concentrationconcentrated
  6. customThe crude mixture is then purified by flash chromatography
  7. additiona mixture of ethyl acetate-hexanes as the eluting medium
  8. customto afford the

Sources & evidence

ORD record
ord-7367dbe50b454478bebd581218e43461
Source dataset
uspto-grants-2012_07
Patent number
US08226929B2

Reaction notes

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