Potassium Carbonate → HCID 59069401, compound
Reaction equation
C([O:4][C@@:5]1([C:9]2[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][CH:10]=2)[C@H:7]([CH3:8])[O:6]1)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO>[Br:15][C:12]1[CH:11]=[CH:10][C:9]([C:5](=[O:4])[C@H:7]([OH:6])[CH3:8])=[CH:14][CH:13]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A 50 mL round bottom flask equipped with a magnetic stir bar, nitrogen gas inlet, and thermocouple was charged with (2S,3S)-2-(4-bromophenyl)-3-methyloxiran-2-yl acetate (490 mg, 1.81 mmol) and methanol (20 mL), and the reaction mixture was cooled to 0° C. in an ice/water bath. Potassium carbonate (15 mg, 0.1 mmol) was added, and the mixture was stirred at 0° C. for 3 hours. The reaction mixture was concentrated and purified by column chromatography to give the product as an oil (208 mg, 50%): 1H NMR (CDCl3) δ 7.79 (d, 2H, J=8.4 Hz), 7.65 (d, 2H, J=8.8 Hz), 5.10 (q, 1H, J=7.0 Hz), 3.73 (bs, 1H), 1.44 (d, 3H, J=7.0Hz).
Workup
- customA 50 mL round bottom flask equipped with a magnetic stir bar, nitrogen gas inlet
- concentrationThe reaction mixture was concentrated
- custompurified by column chromatography
Sources & evidence
- ORD record
- ord-c5c8787c12a747f495552ddba4fd8953
- Source dataset
- uspto-grants-2003_06
- Patent number
- US06573286B1
Reaction notes
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