Tetrahydrofuran → 1,1-Bis(4-dimethylaminophenyl)-2-(diphenylphosphino)propene
Reaction equation
[CH3:1][N:2]([CH3:22])[C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:13]2[CH:18]=[CH:17][C:16]([N:19]([CH3:21])[CH3:20])=[CH:15][CH:14]=2)=[C:10](Br)[CH3:11])=[CH:5][CH:4]=1.C1COCC1.C([Li])CCC.Cl[P:34]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>O>[CH3:1][N:2]([CH3:22])[C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:13]2[CH:18]=[CH:17][C:16]([N:19]([CH3:21])[CH3:20])=[CH:15][CH:14]=2)=[C:10]([P:34]([C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH3:11])=[CH:5][CH:4]=1Participants
Conditions
- Temperature
- -60 °C
Procedure
Into a reactor were introduced 3.0 g (8.3 mmol) of the 1,1-bis(4-dimethylaminophenyl)-2-bromopropene and 10 mL of THF under a nitrogen atmosphere. The contents were cooled to −60° C. Thereto was gradually added dropwise 5.2 mL (8.3 mmol; 1.6 M hexane solution) of butyllithium. The resultant mixture was stirred for 30 minutes. Thereafter, 1.1 mL (6.0 mmol) of chlorodiphenylphosphine was added thereto and this mixture was heated to room temperature and stirred for 16 hours. Water was added to the reaction mixture. The resultant mixture was extracted with ethyl acetate, and the extract was dried with anhydrous magnesium sulfate. Thereafter, the solvent was removed under reduced pressure. The concentrate was recrystallized twice from hexane/ethanol to obtain 1.9 g (60%) of the target compound as white crystals.
Workup
- temperaturethis mixture was heated to room temperature
- extractionThe resultant mixture was extracted with ethyl acetate
- dry with materialthe extract was dried with anhydrous magnesium sulfate
- customThereafter, the solvent was removed under reduced pressure
- customThe concentrate was recrystallized twice from hexane/ethanol
Sources & evidence
- ORD record
- ord-807e04636f8e4173995de69f9ad973c4
- Source dataset
- uspto-grants-2002_09
- Patent number
- US06455720B1
Reaction notes
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