Imidazole → (S)-1-((Tert-butyldimethylsilyl)oxy)propan-2-OL

HRID 339006Notes

Reaction equation

HRID 339006 reaction equation
[CH2:1]([OH:5])[C@@H:2]([OH:4])[CH3:3].[Si:6](Cl)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].N1C=CN=C1.CN(C)C=O>C(OCC)(=O)C>[Si:6]([O:5][CH2:1][C@@H:2]([OH:4])[CH3:3])([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 439846(S)-propane-1,2-diol

Product 1

HCID 13175136(S)-1-((Tert-butyldimethylsilyl)oxy)propan-2-OLYield 105.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of (S)-propane-1,2-diol (1.9 mL, 26 mmol), tert-butyldimethylsilyl chloride (4.87 g, 32 mmol), and imidazole (4.5 g, 66 mmol) in anhydrous dimethylformamide (6.6 mL, 26 mmol) was allowed to stir at ambient temperature for 12 hours. The reaction mixture was poured into ethyl acetate (50 mL) and washed sequentially with saturated aqueous sodium bicarbonate (30 mL) and water (30 mL). The organic extract was dried over sodium sulfate, filtered and concentrated under reduced pressure to give the title compound (5.2 g, 104%) which was used without further purification.

Workup

  1. washwashed sequentially with saturated aqueous sodium bicarbonate (30 mL) and water (30 mL)
  2. extractionThe organic extract
  3. dry with materialwas dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-940434616389414b9b3b96317bf64356
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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