Potassium Carbonate → (1S,2S)-(-)-1-Phenylpropylene oxide
Reaction equation
[CH3:1]/[CH:2]=[CH:3]/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH:10]OS([O-])=O.[K+].C([O-])([O-])=O.[K+].[K+]>C(#N)C.C(N(CC([O-])=O)CC(O)=O)CN(CC([O-])=O)CC(O)=O.[Na+].[Na+].S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH3:1][C@@H:2]1[O:10][C@H:3]1[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- -10 °C
Procedure
Reaction at −10° C.: trans-β-methylstyrene (0.181 g, 1 mmol) was dissolved in acetonitrile/DMM (15 mL, ½, V/V). Buffer (10 mL, 0.05 M solution of Na2B4O7H2O in 4×10−4 M aqueous Na2EDTA), tetrabutylammonium hydrogen sulfate (15 mg, 0.04 mmol), and ketone 1 (0.0774 g, 0.3 mmol) were added with stirring. The mixture was cooled to about −10° C. (inside) (outside temperature was about −12° C. to −15° C.) via a NaCl-ice bath. A solution of Oxone® (0.85 g, 1.38 mmol) in aqueous Na2EDTA (4×10−4 M, 6.5 mL) and a solution of K2CO3 (0.8 g, 5.8 mmol) in water (6.5 mL) were added dropwise separately over a period of 2 h (via syringe pumps or addition funnels). The reaction was then worked up by the same procedure as Method B to afford trans-β-methylstyrene oxide (0.126 g, 94% yield, 95.5%ee).
Workup
- customReaction at −10° C.
- addition(via syringe pumps or addition funnels)
Sources & evidence
- ORD record
- ord-386e59524e72495881cb21407b0fb8e2
- Source dataset
- uspto-grants-2002_02
- Patent number
- US06348608B1
Reaction notes
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