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

HRID 1720683Notes

Reaction equation

HRID 1720683 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-09fc1ae288f64b5a973d6e41c1119f89
Source dataset
uspto-grants-1996_04
Patent number
US05506356

Reaction notes

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