Dimethyl Sulfoxide → (+)-trans-3-Formyl-4-phenylcyclopentan-1-one
Reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH2:12][C@H:13]1[C@H:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:16][C:15](=[O:24])[CH2:14]1.C(N(C(C)C)CC)(C)C>C(Cl)Cl.O>[CH:12]([C@H:13]1[C@H:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:16][C:15](=[O:24])[CH2:14]1)=[O:11]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -70 °C
Procedure
To a solution of oxalyl chloride (0.352 mL, 0.512 g, 4.03 mmol) in methylene chloride (8 mL) at −70° C. was added dropwise DMSO (0.573 mL, 0.630 g, 8.06 mmol). After 10 min, a solution of (+)-trans-3-hydroxymethyl-4-phenylcyclopentan-1-one from Example 11, Step F (0.153 g, 0.807 mmol) in methylene chloride (1 mL) was added dropwise. The reaction mixture was stirred at −70° C. for 45 min and then diisopropylethylamine (2.1 mL, 1.6 g, 4.48 mmol) was added. The reaction mixture was allowed to warm to rt for 10 min and then diluted with methylene chloride, poured into water, and extracted three times with methylene chloride. The organic layers were combined, washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude title compound (0.15 g) was used directly in Step B.
Workup
- temperatureto warm to rt for 10 min
- extractionextracted three times with methylene chloride
- washwashed with brine
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-81240fd29b0644689b861ae0c90fcb60
- Source dataset
- uspto-grants-2002_08
- Patent number
- US06432981B1
Reaction notes
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