Imidazole → Benzyl 3-{[tert-butyl(dimethyl)silyl]oxy}cyclopentanecarboxylate

HRID 1160612Notes

Reaction equation

HRID 1160612 reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:3]1.N1C=CN=C1.[Si:22](Cl)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23].O>CN(C=O)C.CCOC(C)=O>[Si:22]([O:1][CH:2]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:8])[CH2:3]1)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 14530758Benzyl 3-hydroxycyclopentanecarboxylate

Product 1

HCID 68717013Benzyl 3-{[tert-butyl(dimethyl)silyl]oxy}cyclopentanecarboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of benzyl 3-hydroxycyclopentanecarboxylate (1.0 g, 4.54 mmol) in 9 ml of degassed DMF was added imidazole (0.34 g, 4.99 mmol) and tert-butyldimethylsilyl chloride (0.75 g, 4.99 mmol). The mixture was stirred at ambient temperature for 4 hours, and then poured into 70 mL of water, and extracted with ethyl acetate. The combined ethyl acetate extracts were washed with water and brine and then dried over sodium sulfate. Filtration and concentration afforded the crude product which was subjected to chromatography on silica gel eluting with 5% EtOAc in hexanes to give benzyl 3-{[tert-butyl(dimethyl)silyl]oxy}cyclopentanecarboxylate.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined ethyl acetate extracts were washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationFiltration and concentration
  5. customafforded the crude product which

Sources & evidence

ORD record
ord-fe3af9218aee4e8d81d4a254c58e43b1
Source dataset
uspto-grants-2010_10
Patent number
US07816380B2

Reaction notes

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