Imidazole → (2R)-1-{[(1,1-Dimethylethyl)(dimethyl)silyl]oxy}propan-2-ol

HRID 493371

Reaction equation

HRID 493371 reaction equation
[C:1]([Si:5]([CH3:8])([CH3:7])Cl)([CH3:4])([CH3:3])[CH3:2].[CH2:9]([OH:13])[C@H:10]([OH:12])[CH3:11].N1C=CN=C1>ClCCl>[O:13]([CH2:9][C@H:10]([OH:12])[CH3:11])[Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 259994R-(-)-1,2-Propanediol

Product 1

HCID 13175135(2R)-1-{[(1,1-Dimethylethyl)(dimethyl)silyl]oxy}propan-2-olYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of tert-butyldimethylchlorosilane (9.9 g, 65.7 mmol) in dichloromethane was added dropwise to a solution of (R)-(−)-1,2-propanediol (5 g, 65.7 mmol) and imidazole (4.47 g, 65.7 mmol) in anhydrous dichloromethane at 0° C. The reaction mixture was stirred at 0° C. for 30 min before dilution with dichloromethane. The solution was washed with water three times followed by the addition of brine. The organic layer was separated, dried through a MgSO4 pad and concentrated under reduced pressure to afford 12.0 g (96%) of (2R)-1-(tert-Butyldimethylsiloxy)propan-2-ol.

Workup

  1. washThe solution was washed with water three times
  2. additionfollowed by the addition of brine
  3. customThe organic layer was separated
  4. dry with materialdried through a MgSO4 pad
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7aeeb593719a4b0ea9601e19858f3838
Source dataset
uspto-grants-2009_05
Patent number
US07534813B2

Linked notes

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