2-Methylbenzenesulfonic acid hydrate → 5-(4-Chlorobenzyl)-2-chloromethyl-2-methyl-cyclopentanone
Reaction equation
COC([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:12])([CH3:10])[C:6]1=[O:13])=O.O.C1(C)C(S(O)(=O)=O)=CC=CC=1>O>[Cl:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][CH:5]2[C:6](=[O:13])[C:7]([CH2:11][Cl:12])([CH3:10])[CH2:8][CH2:9]2)=[CH:20][CH:19]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 120 °C
Procedure
To 1.00 g of Compound 3-1-3 synthesized in Production Example 4, 0.578 g of toluenesulfonic acid monohydrate and 100 mg of water were added, and the resulting mixture was stirred in an oil bath of 120° C. for 1.5 hours. After the reaction, water was added to the reaction solution thus obtained, and extraction with ethyl acetate was then carried out. The extract was washed with an aqueous solution of sodium hydrogen carbonate and saturated brine. After the organic layer was dried over anhydrous sodium sulfate, the solvent was distilled away. The residue was purified by silica gel column chromatography to obtain 752 mg of Compound 4-1-3.
Workup
- additionwere added
- additionwas added to the reaction solution
- customthus obtained
- extractionextraction with ethyl acetate
- washThe extract was washed with an aqueous solution of sodium hydrogen carbonate and saturated brine
- dry with materialAfter the organic layer was dried over anhydrous sodium sulfate
- distillationthe solvent was distilled away
- customThe residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-e83c17d032ee49ad9eed6a208d26cd9d
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09278966B2
Reaction notes
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