Sodium Bicarbonate → HCID 23103592, compound
Reaction equation
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH:13]1([C:16]2[CH:21]=[CH:20][C:19]([C:22]([C:24]3[CH:29]=[CH:28][N:27]=[CH:26][C:25]=3[O:30]COCC[Si](C)(C)C)=[O:23])=[CH:18][CH:17]=2)[CH2:15][CH2:14]1.C(=O)([O-])O.[Na+]>C1COCC1>[CH:13]1([C:16]2[CH:17]=[CH:18][C:19]([C:22]([C:24]3[CH:29]=[CH:28][N:27]=[CH:26][C:25]=3[OH:30])=[O:23])=[CH:20][CH:21]=2)[CH2:14][CH2:15]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
p-Toluenesulfonic acid monohydrate (3.03 g, 15.9 mmol) was added to a solution of (4-cyclopropylphenyl)-[3-(2-trimethylsilylethoxymethoxy)pyridin-4-yl]methanone (1.96 g, 5.30 mmol) in THF (49 mL) and the mixture solution was stirred at 65° C. for one hour. The reaction mixture was cooled to room temperature and a saturated sodium hydrogencarbonate aqueous solution was added thereto and the mixture was extracted with ether, and the organic layer was dried over anhydrous magnesium sulfate. After filtration, the solvent was distilled under reduced pressure, and the obtained residue was purified by silica gel flash column chromatography [developing solution=n-hexane:ethyl acetate (2:3)] to obtain the title product (1.10 g, 87%).
Workup
- temperatureThe reaction mixture was cooled to room temperature
- extractionthe mixture was extracted with ether
- dry with materialthe organic layer was dried over anhydrous magnesium sulfate
- filtrationAfter filtration
- distillationthe solvent was distilled under reduced pressure
- customthe obtained residue was purified by silica gel flash column chromatography [developing solution=n-hexane:ethyl acetate (2:3)]
Sources & evidence
- ORD record
- ord-8ac2b3a6fd94470389726009f5d0c28d
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08048897B2
Reaction notes
Loading…