Boron trifluoride etherate → (-)-Benzyl (R)-glycidyl ether
Reaction equation
C([Li])[CH2:2][CH2:3][CH3:4].CP(=O)(OCC)OCC.B(F)(F)F.C[CH2:20][O:21][CH2:22][CH3:23].[O:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1>>[CH2:28]([O:24][CH2:23][C@H:22]1[CH2:20][O:21]1)[C:27]1[CH:4]=[CH:3][CH:2]=[CH:25][CH:26]=1Participants
Conditions
- Temperature
- -78 °C
Procedure
A solution of n-butyllithium (2.5M in hexane, 72 mL, 180 mmol) was added dropwise to a solution of diethyl methylphosphonate (27.4 g, 180 mmol) in 200 mL dry tetrahydrofuran (THF) at -78° C. After 30 minutes of stirring at -78° C., the resulting white suspension was added in a slow stream through a cannula to a stirred solution of BF3.Et2O (22.13 mL, 180 mmol) in THF (400 mL) at -78° C. After 10 minutes, neat (R)-(-)-2-(benzyloxymethyl)oxirane 1-1 (10 g, 61 mmol, obtained from the Aldrich Chemical Co.) was added quickly to this suspension. The reaction mixture was stirred for 30 minutes at -78° C., quenched by adding saturated aqueous NaHCO3 (100 mL) and allowed to warm to room temperature. The reaction was diluted with 450 mL of ether and washed with 2×200 mL of saturated sodium bicarbonate solution and 100 mL of brine. The ether layers were dried (MgSO4) and evaporated. The residue was chromatographed on silica gel, eluting with 5% methanol/95% dichloromethane to give the product 1-2 as a pale yellow oil (18.0 g, 94%).
Workup
- waitAfter 10 minutes
Sources & evidence
- ORD record
- ord-03706d9023a841e0ab038228ec49d92a
- Source dataset
- uspto-grants-1999_03
- Patent number
- US05877166
Reaction notes
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