Imidazole → (R)-(-)-1-(tert-butyldimethylsilanyloxy)-3-chloropropan-2-ol

HRID 2221405Notes

Reaction equation

HRID 2221405 reaction equation
[Cl:1][CH2:2][C@H:3]([OH:6])[CH2:4][OH:5].[C:7]([Si:11]([CH3:14])([CH3:13])Cl)([CH3:10])([CH3:9])[CH3:8].N1C=CN=C1>CN(C)C=O>[Si:11]([O:5][CH2:4][C@@H:3]([OH:6])[CH2:2][Cl:1])([C:7]([CH3:10])([CH3:9])[CH3:8])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 148793(2R)-3-Chloro-1,2-propanediol

Product 1

HCID 86604379(R)-(-)-1-(tert-butyldimethylsilanyloxy)-3-chloropropan-2-olYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To N,N-dimethylformamide (40 ml) solution of (R)-(−)-3-chloro-1,2-propanediol (7 g), under ice-cooling and stirring condition, were added tert-butyldimethylchlorosilane (10.6 g) and imidazole (5.2 g), then stirred at a room temperature overnight. Ice-water (120 ml) was added to the reaction mixture, and extracted with ethyl acetate (50 ml) 3 times, the extracts were combined together and washed with an aqueous solution being saturated with sodium chloride, then dried over anhydrous magnesium sulfate. After being filtrated under a reduced pressure, the filtrate was concentrated, there was obtained (R)-(−)-1-(tert-butyldimethylsilanyloxy)-3-chloropropan-2-ol (13.24 g, yield: 92.4%) as colorless liquid product.

Workup

  1. stirringstirred at a room temperature overnight
  2. extractionextracted with ethyl acetate (50 ml) 3 times
  3. washwashed with an aqueous solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter being filtrated under a reduced pressure
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-cad2adc019564267ab9179a3cb906184
Source dataset
uspto-grants-2008_05
Patent number
US07368579B2

Reaction notes

Loading…