Bromochloromethane → Methyl 2-chloromethyl-2,6-bis(benzylideneamino)hexanoate
Reaction equation
C([N-]C(C)C)(C)C.[Li+].C([Li])CCC.[CH:14](=[N:21][CH:22]([CH2:27][CH2:28][CH2:29][CH2:30][N:31]=[CH:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:23]([O:25][CH3:26])=[O:24])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Cl:39][CH2:40]Br>O1CCCC1.CCCCCC.CN(C)P(N(C)C)(N(C)C)=O>[Cl:39][CH2:40][C:22]([N:21]=[CH:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)([CH2:27][CH2:28][CH2:29][CH2:30][N:31]=[CH:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:23]([O:25][CH3:26])=[O:24]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
To a solution of lithium diisopropylamide (10 mmol) prepared in situ from a solution of 1N diisoproppylamine in tetrahydrofuran (THF) and a solution of butyl lithium (2N) in hexane and hexamethylphosphoramide (HMPA) (2.5 ml) in THF cooled to -78° C., magnetically stirred, and kept under nitrogen, is added slowly a solution of methyl 2,6-bis(benzylideneamino)hexanoate (3.365 g, 10 mmol) in dry THF (20 ml). The reaction mixture is stirred at -78° C. for 1/2 hour, and then a solution of chlorobromomethane (1.3 g, about 10 mmol) in dry THF (10 ml) is added rapidly. The temperature is allowed to rise slowly to room temperature, and the stirring is continued overnight. The reaction mixture is quenched with water and extracted with ether. The ether extract is washed with water and concentrated at reduced pressure to give methyl 2-chloromethyl-2,6-bis(benzylideneamino)hexanoate as an oily residue.
Workup
- stirringThe reaction mixture is stirred at -78° C. for 1/2 hour
- customto rise slowly to room temperature
- customThe reaction mixture is quenched with water
- extractionextracted with ether
- extractionThe ether extract
- washis washed with water
- concentrationconcentrated at reduced pressure
Sources & evidence
- ORD record
- ord-04bd1445f8124c299a7b22c8cee4c038
- Source dataset
- uspto-grants-1988_05
- Patent number
- US04743691
Reaction notes
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