Imidazole → HCID 14134379, compound

HRID 1651662Notes

Reaction equation

HRID 1651662 reaction equation
[OH:1][C@@H:2]1[CH2:7][O:6][C@@H:5]([CH3:8])[O:4][C@H:3]1[CH2:9][OH:10].[C:11]([Si:15]([CH3:18])([CH3:17])Cl)([CH3:14])([CH3:13])[CH3:12].N1C=CN=C1>CN(C)C=O.C(OCC)(=O)C>[O:10]([CH2:9][C@H:3]1[C@H:2]([OH:1])[CH2:7][O:6][C@@H:5]([CH3:8])[O:4]1)[Si:15]([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:18])[CH3:17]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 14134376HCID 14134376, compound

Product 1

HCID 14134379HCID 14134379, compoundYield 105.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (2R,4S,5R)-5-hydroxy-4-hydroxymethyl-2-methyl-1,3-dioxane (13.0 g), t-butyldimethylchlorosilane (14.5 g) and imidazol (13.1 g) in N,N-dimethylformamide (130 ml) was stirred at room temperature for 2 hours and the mixture was diluted with ethyl acetate (500 ml). The solution was washed successively with water, diluted hydrochloric acid, saturated aqueous sodium hydrogen carbonate and brine and dried over magnesium sulfate. The solvent was evaporated in vacuo to give (2R,4S,5R)-4-t-butyldimethylsiloxymethyl-5-hydroxy-2-methyl-1,3-dioxane (24.2 g) as a colorless oil.

Workup

  1. washThe solution was washed successively with water, diluted hydrochloric acid, saturated aqueous sodium hydrogen carbonate and brine
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-83d6049678e04ce29b1b892c76ee1d99
Source dataset
uspto-grants-1990_05
Patent number
US04929639

Reaction notes

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