Reaction equation
C(Cl)(=O)C([Cl:4])=O.[C:7]([N:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH:12]=O)([CH3:10])([CH3:9])[CH3:8].[C:20]([N:24]([Si](C)(C)C)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([CH3:23])([CH3:22])[CH3:21]>C1(C)C=CC=CC=1>[Cl-:4].[C:7]([N:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH:12]=[N+:24]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([CH3:10])([CH3:9])[CH3:8]Participants
Procedure
Oxalyl chloride (0.42 mL, 5.0 mmol) was added dropwise to a solution of 2a (0.582 g, 3.28 mmol) in toluene (10 mL) at −78° C. The reaction mixture was stirred for 2 h at room temperature. After evaporation of all the volatiles by vacuum, CH2Cl2 (10 mL) was added. 3a (0.778 g, 3.50 mmol) was added to the reaction solution at −78° C., and the reaction mixture was slowly warmed to room temperature for 30 min. After stirring for 3 h at room temperature, the reaction solution was concentrated to 2 mL. The solution was dropped to a rapidly stirred hexanes (10 mL). The precipitated solid was collected and was washed with hexane (10 mL×2) to give 4a (1.028 g, 90.8%) as a white solid. 1H NMR (300 MHz, CDCl3) δ 8.90 (s, 1H), 7.11-6.78 (m, 10H), 1.56 (s, 18H); 13C NMR (75 MHz, CDCl3) δ 153.8, 136.1, 130.3, 128.9, 66.2, 29.7. HRMS-ESI (m/z): [M]+ calcd for C21H29ClN2, 309.2325. found, 309.2322.
Workup
- customAfter evaporation of all the volatiles by vacuum, CH2Cl2 (10 mL)
- additionwas added
- temperaturethe reaction mixture was slowly warmed to room temperature for 30 min
- stirringAfter stirring for 3 h at room temperature
- concentrationthe reaction solution was concentrated to 2 mL
- additionThe solution was dropped to a rapidly stirred hexanes (10 mL)
- customThe precipitated solid was collected
- washwas washed with hexane (10 mL×2)
Sources & evidence
- ORD record
- ord-938252560db04c57b5041358e635052c
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08530687B2
Linked notes
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