Imidazole → (2S,3S)-4-benzyloxy-2,3-epoxy-1-butanol tert-butyldimethylsilyl ether

HRID 1109421Notes

Reaction equation

HRID 1109421 reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]1[O:14][C@H:11]1[CH2:12][OH:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.[C:20]([Si:24]([CH3:27])([CH3:26])Cl)([CH3:23])([CH3:22])[CH3:21]>CN(C=O)C.C(OCC)(=O)C>[Si:24]([O:13][CH2:12][C@@H:11]1[O:14][C@H:10]1[CH2:9][O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:27])[CH3:26]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 10171312(2S,3S)-3-((Phenylmethoxy)methyl)-2-oxiranemethanol

Product 1

HCID 15708218(2S,3S)-4-benzyloxy-2,3-epoxy-1-butanol tert-butyldimethylsilyl etherYield 67.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.15 g of (2S,3S)-4-benzyloxy-2,3-epoxy-1-butanol was dissolved in 13 ml of dry DMF, and 1.83 g of imidazole and 2 g of tert-butyldimethylchlorosilane were added thereto. The mixture was stirred at room temperature overnight. The reaction solution was diluted with ethyl acetate, washed sequentially with cold 1N hydrochloric acid, water and a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=10/1) to obtain 2.3 g of (2S,3S)-4-benzyloxy-2,3-epoxy-1-butanol tert-butyldimethylsilyl ether as colorless oily substance.

Workup

  1. washwashed sequentially with cold 1N hydrochloric acid, water
  2. dry with materiala saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate
  3. distillationThen, the solvent was distilled off under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-aa544ba3cbeb4bd5a5836082f2b3ac34
Source dataset
uspto-grants-1994_06
Patent number
US05319082

Reaction notes

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