Imidazole → HCID 18953728, compound

HRID 1492004Notes

Reaction equation

HRID 1492004 reaction equation
Cl.[OH:2][CH:3]1[CH2:7][O:6][CH:5]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[CH:4]1[CH2:14][CH2:15][CH2:16][OH:17].[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19].N1C=CN=C1>CN(C)C=O>[Si:18]([O:17][CH2:16][CH2:15][CH2:14][CH:4]1[CH:3]([OH:2])[CH2:7][O:6][CH:5]1[C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 18953753HCID 18953753, compound

Product 1

HCID 18953728HCID 18953728, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 10 g (0.0448 mole) of 4-hydroxy-3-(3-hydroxyprop-1-yl)-2-(3-pyridyl)tetrahydrofuran hydrochloride, 7.68 g (0.048 mole) of t-butyldimethylsilyl chloride and 6.86 g (0.0977 mole) of imidazole in 105.8 ml of dimethylformamide is stirred at room temperature for 15 h and evaporated. The residue is triturated with ethyl acetate and washed with water and brine, dried (MgSO4) and evaporated. The residue is purified by flash chromatography using methylene chloride-ethyl acetate-methanol (20:4:1) to give 3-(3-t-butyldimethylsilyloxyprop-1-yl)-4-hydroxy-2-(3-pyridyl)tetrahydrofuran as an oil.

Workup

  1. customevaporated
  2. customThe residue is triturated with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-bbd045a2407b49738aba31a36471527a
Source dataset
uspto-grants-1994_12
Patent number
US05371096

Reaction notes

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