Dimethylformamide → 1-(4-Chlorobenzyl)-3-chloromethyl-3-methyl-2-oxo-cyclopentancarboxylic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3]([C:5]1([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[CH2:9][CH2:8][C:7]([CH2:11]O)([CH3:10])[C:6]1=[O:13])=[O:4].S(Cl)([Cl:24])=O.CN(C=O)C>O>[CH3:1][O:2][C:3]([C:5]1([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[CH2:9][CH2:8][C:7]([CH2:11][Cl:24])([CH3:10])[C:6]1=[O:13])=[O:4]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
To 8.79 g of Compound 2-1 obtained in Production Example 1, 3.04 ml of thionyl chloride and 0.15 ml of DMF were added. The resulting mixture was stirred in an oil bath of 90° C. for 2.5 hours. After the reaction, water was added to the reaction solution thus obtained, and extraction with toluene was carried out. The organic layer thus extracted was washed with a saturated aqueous solution of sodium carbonate and saturated brine and then dried over anhydrous sodium sulfate. The solvent was distilled away, and the residue was then purified by silica gel column chromatography to obtain 6.57 g of Compound 3-1-3.
Workup
- additionwere added
- additionwas added to the reaction solution
- customthus obtained
- extractionextraction with toluene
- extractionThe organic layer thus extracted
- washwas washed with a saturated aqueous solution of sodium carbonate and saturated brine
- dry with materialdried over anhydrous sodium sulfate
- distillationThe solvent was distilled away
- customthe residue was then purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-23a8b54f794e424a8554a60c01e4a5d7
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09278966B2
Reaction notes
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