Formaldehyde → 1-(4-Chlorobenzyl)-3-hydroxymethyl-3-methyl-2-oxocyclopentanecarboxylic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3]([C:5]1([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[CH2:9][CH2:8][CH:7]([CH3:10])[C:6]1=[O:11])=[O:4].C=O.[C:22](=O)([O-])[O-:23].[K+].[K+]>O>[CH3:1][O:2][C:3]([C:5]1([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)[CH2:9][CH2:8][C:7]([CH2:22][OH:23])([CH3:10])[C:6]1=[O:11])=[O:4]Participants
5
Procedure
To 1.12 g of 1-(4-chlorobenzyl)-3-methyl-2-oxo-cyclopentancarboxylic acid methyl ester (Compound 1-1), which is a known compound, 0.90 ml of 37% aqueous solution of formaldehyde and 276 mg of potassium carbonate were added, and the resulting mixture was vigorously stirred at room temperature for 4 hours. After the reaction, water was added to the reaction solution thus obtained, and extraction with ethyl acetate was then carried out. The organic layer thus extracted was washed with 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 1.180 g of Compound 2-1.
Workup
- additionwere added
- additionwas added to the reaction solution
- customthus obtained
- extractionextraction with ethyl acetate
- extractionThe organic layer thus extracted
- washwas washed with 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-f0850863324642f2b593a145f8c7c41e
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09278966B2
Reaction notes
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