1-Bromo-1-chloroethane → Methyl 2-chloromethyl-2,6-bis(benzylideneamino)hexanoate

HRID 1607746Notes

Reaction equation

HRID 1607746 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][CH:40](Br)C>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

8

Reactant 4

HCID 116541-Bromo-1-chloroethaneHCID 2724682Lithium diisopropylamideHCID 14231031Methyl 2,6-bis(benzylideneamino)hexanoateHCID 178418339Butyllithium

Product 1

HCID 14231032Methyl 2-chloromethyl-2,6-bis(benzylideneamino)hexanoate

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent4×HCID 8058HexaneSolventHCID 12679HexamethylphosphoramideSolvent

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 chlorobromoethane (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

  1. stirringThe reaction mixture is stirred at -78° C. for 1/2 hour
  2. customto rise slowly to room temperature
  3. customThe reaction mixture is quenched with water
  4. extractionextracted with ether
  5. extractionThe ether extract
  6. washis washed with water
  7. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-5d23e8d5d0bf4a6fae96f85f5a24cb83
Source dataset
uspto-grants-1989_09
Patent number
US04866206

Reaction notes

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