Imidazole → (R)-tert-Butyldimethyl(oxiran-2-ylmethoxy)silane

HRID 1259267Notes

Reaction equation

HRID 1259267 reaction equation
[CH2:1]1[O:3][C@H:2]1[CH2:4][OH:5].[CH3:6][C:7]([Si:10](Cl)([CH3:12])[CH3:11])([CH3:9])[CH3:8].N1C=CN=C1>C(Cl)Cl.CN(C=O)C.C(Cl)Cl>[C:7]([Si:10]([CH3:12])([CH3:11])[O:5][CH2:4][C@H:2]1[CH2:1][O:3]1)([CH3:9])([CH3:8])[CH3:6]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 6973630(-)-Glycidol

Product 1

HCID 11008692(R)-tert-Butyldimethyl(oxiran-2-ylmethoxy)silane

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 22350042dichloromethane N,N-dimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of (S)-glycidol (2.5 g, 33.7 mmol) in 100 mL of 1:1 DCM/DMF was cooled to 0° C. and treated with TBDMS-Cl (6.10 g, 40.5 mmol) and imidazole (3.45 g, 50.6 mmol). The mixture was stirred overnight at 0° C. Solution was diluted with DCM and washed with saturated aqueous NaHCO3 and brine, dried over Na2SO4 and concentrated to provide A-1 as a colorless oil. Data for A-1: LRMS m/z (M+H)=189.21 found; 189.34 required

Workup

  1. washwashed with saturated aqueous NaHCO3 and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customto provide A-1 as a colorless oil

Sources & evidence

ORD record
ord-1f7387fc9ad44240a768827be4248542
Source dataset
uspto-grants-2013_06
Patent number
US08466281B2

Reaction notes

Loading…