Dichloromethane → methyl 2,2-dimethyl-3-phenyl-3-(3-phenyl-1H-indazol-6-yl)propanoate
Reaction equation
[C:1]1([CH:7]([C:9]2[CH:17]=[C:16]3[C:12]([C:13]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[N:14][NH:15]3)=[CH:11][CH:10]=2)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO[C:26](O[Si](C)(C)C)=[C:27](C)[CH3:28].[C:35](=[O:38])(O)[O-:36].[Na+].Cl[CH2:41]Cl>>[CH3:26][C:27]([CH3:28])([CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:9]1[CH:17]=[C:16]2[C:12]([C:13]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[N:14][NH:15]2)=[CH:11][CH:10]=1)[C:35]([O:36][CH3:41])=[O:38]Participants
5
Conditions
- Temperature
- 0 °C
Procedure
To a stirred solution of phenyl(3-phenyl-1H-indazol-6-yl)methanol (67 mg, 0.22 mmol) and (1-methoxy-2-methylprop-1-enyloxy)trimethylsilane (2 mL) in anhydrous dichloromethane (4 mL) was added boron trifluoride diethyl ether complex (0.2 mL, 1.6 mmol) dropwise at 0° C. under argon. After stirred at 0° C. for 15 min, rt for 2 hr, and 40° C. for 1.5 hr, the mixture was poured into saturated aqueous sodium bicarbonate solution at 0° C. The mixture was stirred well and extracted with dichloromethane (10 mL). The dichloromethane layer was dried (Na2SO4) and concentrated. Silica gel flash chromatography gave methyl 2,2-dimethyl-3-phenyl-3-(3-phenyl-1H-indazol-6-yl)propanoate (45 mg, 0.12 mmol, 53% yield) as a glassy solid.
Workup
- wait40° C. for 1.5 hr
- stirringThe mixture was stirred well
- extractionextracted with dichloromethane (10 mL)
- dry with materialThe dichloromethane layer was dried (Na2SO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-cbe2be6ac8d84dddba9a40319f9c8e36
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08067447B2
Reaction notes
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