Sodium Sulfite → (2R)-1-(3-Chlorophenyl)-2-hydroxypropan-1-one
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([O:11][Si](C(C)(C)C)(C)C)=[CH:9][CH3:10])[CH:5]=[CH:6][CH:7]=1.CS(N)(=O)=[O:21].S([O-])([O-])=O.[Na+].[Na+]>C(O)(C)(C)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:8](=[O:11])[C@H:9]([OH:21])[CH3:10])[CH:5]=[CH:6][CH:7]=1Participants
5
Conditions
- Temperature
- 0 °C
Procedure
Z-1-(3-Chlorophenyl-tert-butyldimethylsilyloxy-1-propene (12.0 g, 44 mmol) was added to a well-stirred mixture of AD-mix-P (80 g) and CH3SO2NH2 (4.2 g, 44 mmol) in tert-butyl alcohol/water mixture (220 mL/220 mL) maintained at 0° C. The reaction mixture was stirred at 0° C. for 28 hours. Solid sodium sulfite (40 g) was added. The mixture was stirred for an additional 45 minutes and extracted with CH2Cl2 (2×100 mL). The combined organic extracts were washed with NaHCO3 and brine, and evaporated. The residue was passed through a silica gel column to give the desired product (7.0 g). 1H NMR (CDCl3): δ 1.45 (d, 3H), 5.15 (q, 1H), 7.2-7.9 (m, 4H).
Workup
- stirringThe mixture was stirred for an additional 45 minutes
- extractionextracted with CH2Cl2 (2×100 mL)
- washThe combined organic extracts were washed with NaHCO3 and brine
- customevaporated
Sources & evidence
- ORD record
- ord-6c1b42bb5a5e4d96a944731954c405f0
- Source dataset
- uspto-grants-2002_01
- Patent number
- US06342496B1
Reaction notes
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