2,2,2-Trichloroethyl chloroformate → HCID 44216388, compound
Reaction equation
[Cl:1][C:2]([Cl:9])([Cl:8])[CH2:3][O:4][C:5](Cl)=[O:6].[CH3:10][C@@H:11]1[N:34]([CH3:35])[CH2:33][C@:16]23[CH2:17][CH2:18][C@@H:19]4[C@@:24]5([CH3:32])[CH2:25][CH2:26][C@H:27]([N:29](C)[CH3:30])[CH2:28][C:23]5=[CH:22][CH2:21][C@H:20]4[C@@H:15]2[CH2:14][CH2:13][C@H:12]13>C1C=CC=CC=1>[Cl:1][C:2]([Cl:9])([Cl:8])[CH2:3][O:4][C:5](=[O:6])[N:29]([CH3:30])[CH:27]1[CH2:28][C:23]2[C:24]([CH3:32])([CH:19]3[CH:20]([CH2:21][CH:22]=2)[CH:15]2[CH2:14][CH2:13][CH:12]4[CH:11]([CH3:10])[N:34]([CH3:35])[CH2:33][C:16]24[CH2:17][CH2:18]3)[CH2:25][CH2:26]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
2,2,2-Trichloroethylchloroformate (5.94 g, 28 mmol) was added dropwise to a stirred solution of conessine (10 g, 28 mmol) in 200 mL benzene. Very thick gel resulted. The mixture was heated at reflux for 4 h (oil bath temperature 90° C.), then cooled down to room temperature, quenched with water, the pH adjusted with 25 mL saturated sodium bicarbonate, and extracted with dichloromethane 3×. Organic layers were dried over Na2SO4, filtered, and evaporated to give crude product, which was purified by flash chromatography to give desired product (8.8 g, 61% yield).
Workup
- customVery thick gel resulted
- temperatureThe mixture was heated
- temperaturecooled down to room temperature
- customquenched with water
- extractionextracted with dichloromethane 3×
- dry with materialOrganic layers were dried over Na2SO4
- filtrationfiltered
- customevaporated
- customto give crude product, which
- customwas purified by flash chromatography
Sources & evidence
- ORD record
- ord-6954f1899fc848e2834337c724c99c0b
- Source dataset
- uspto-grants-2008_03
- Patent number
- US07345034B2
Reaction notes
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