Sodium sulfate decahydrate → HCID 23157461, compound
Reaction equation
[C:1]1([C:7]2[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:9]([CH2:18][C:19]3[CH:28]=[CH:27][C:22]([C:23](OC)=[O:24])=[CH:21][C:20]=3[O:29][CH:30]([CH3:32])[CH3:31])[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[C:1]1([C:7]2[CH:11]=[C:10]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:9]([CH2:18][C:19]3[CH:28]=[CH:27][C:22]([CH2:23][OH:24])=[CH:21][C:20]=3[O:29][CH:30]([CH3:32])[CH3:31])[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1Participants
Conditions
- Temperature
- 0 °C
Procedure
To a solution of methyl 4-[(3,5-diphenyl-1H-pyrazol-1-yl)methyl]-3-isopropoxybenzoate (0.59 g, 1.38 mmol) in tetrahydrofuran (12 mL) was added lithium aluminum hydride (52 mg, 1.38 mmol) with stirring at 0° C., and the mixture was stirred at the same temperature for 2.5 hr. After completion of the reaction, sodium sulfate decahydrate (0.89 g, 2.76 mmol) was added to the reaction mixture, and the mixture was stirred at room temperature for 2 hr. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1-hexane/ethyl acetate=1/1) to give the title compound (0.50 g, yield 92%) as a colorless oil. MS (ESI+): 399 (M+H).
Workup
- stirringthe mixture was stirred at the same temperature for 2.5 hr
- additionwas added to the reaction mixture
- stirringthe mixture was stirred at room temperature for 2 hr
- filtrationThe insoluble material was filtered off
- concentrationthe filtrate was concentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1-hexane/ethyl acetate=1/1)
Sources & evidence
- ORD record
- ord-e521ddfe5258452abea2008398da02aa
- Source dataset
- uspto-grants-2009_04
- Patent number
- US07517910B2
Reaction notes
Loading…