Imidazole → (2R)-1-{[(1,1-Dimethylethyl)(dimethyl)silyl]oxy}propan-2-ol
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=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
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
To a solution of (s)-(+)-1,2-propanediol (2.0 g, 26.3 mmol) in DMF (5 mL) was added TBS-Cl (5.94 g, 39.4 mmol) and imidazole (2.147 g, 31.5 mmol). The reaction was stirred at 25° C. for 18 h. The reaction mixture was partitioned between ethyl acetate and sat. ammonium chloride. The organic phase was washed with sat ammonium chloride and brine, dried (MgSO4) and concentrated in vacuo. The crude product was purified by flash chromatography to give 33A (4.0 g, 80% yield) as a colorless oil.
Workup
- customThe reaction mixture was partitioned between ethyl acetate and sat. ammonium chloride
- washThe organic phase was washed with sat ammonium chloride and brine
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
- customThe crude product was purified by flash chromatography
Sources & evidence
- ORD record
- ord-577185b5166d419bb0c1e9b1f54e6f31
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09174974B2
Reaction notes
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