Allyl bromide → HCID 21564443, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:15][CH2:14][C:13]3[CH:16]=[CH:17][C:18]([OH:20])=[CH:19][C:12]=3[CH2:11][CH2:10][NH:9][CH2:8][C:7]=2[C:21]=1[O:22][CH3:23].[CH2:24](Br)[CH:25]=[CH2:26].C(=O)(O)[O-].[Na+]>O>[CH2:26]([N:9]1[CH2:10][CH2:11][C:12]2[CH:19]=[C:18]([OH:20])[CH:17]=[CH:16][C:13]=2[CH2:14][CH2:15][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[C:21]([O:22][CH3:23])[C:7]=2[CH2:8]1)[CH:25]=[CH2:24]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 100 mg of 3,4-dimethoxy-10-hydroxy-5,6,7,8,13,14-hexahydrodibenz[c,g]azecine, 42.6 ml of allyl bromide and 32.3 mg of sodium bicarbonate in 4 ml of dimethylformaide is stirred for 2 hours at 100°C in argon atmosphere. After cooling, 40 ml of water is added to the mixture, and the mixture is extracted with methylene chloride. The extract is washed with water, dried over anhydrous sodium sulfate, and evaporated to dryness under reduced pressure. The residue is dissolved in benzene, passed through a column of 3.8 g of silica gel, and eluated with benzene - ethyl acetate (10 : 1). The evaporation of the solvent affords 106 mg of 6-allyl-3,4-dimethoxy-10-hydroxy-5,6,7,8,13,14-hexahydrodibenz[c,g]azecine as a colorless oily material. IR: νmaxCHCl 3 3604, 3420 and 1641 cm-1.
Workup
- temperatureAfter cooling
- extractionthe mixture is extracted with methylene chloride
- washThe extract is washed with water
- dry with materialdried over anhydrous sodium sulfate
- customevaporated to dryness under reduced pressure
- dissolutionThe residue is dissolved in benzene
- customThe evaporation of the solvent
Sources & evidence
- ORD record
- ord-17b56aee5c154944a38e59d5e40501f9
- Source dataset
- uspto-grants-1976_01
- Patent number
- US03932384
Reaction notes
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