Chloromethyl Methyl Ether → HCID 21714298, compound

HRID 650080Notes

Reaction equation

HRID 650080 reaction equation
[Cl:1][C:2]1[C:10]([OH:11])=[CH:9][C:8]2[C:12](=[O:17])[CH2:13][CH2:14][CH2:15][CH2:16][N:6]3[C:7]=2[C:3]=1[CH:4]=[C:5]3[C:18]([O:20][CH2:21][CH3:22])=[O:19].[CH3:23][O:24][CH2:25]Cl.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[C:10]([O:11][CH2:23][O:24][CH3:25])=[CH:9][C:8]2[C:12](=[O:17])[CH2:13][CH2:14][CH2:15][CH2:16][N:6]3[C:7]=2[C:3]=1[CH:4]=[C:5]3[C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 11430Potassium CarbonateHCID 21714267HCID 21714267, compound

Product 1

HCID 21714298HCID 21714298, compoundYield 47.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of ethyl 5,6,7,8-tetrahydro-11-chloro-10-hydroxy-8-oxo-4H-azocino[3,2,1-hi]indole-2-carboxylate (0.95 g, 2.93 mmol), chloromethyl methyl ether (0.35 g, 4.40 mmol), potassium carbonate (1.22 g, 8.80 mmol) and N,N-dimethylformamide (25 ml) was stirred at room temperature for 1 hour. The insoluble material was filtered off and the filtrate was poured into ice water and extracted twice with ethyl acetate. The extract solution was washed with a 5% aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=2/98) to obtain 0.51 g of ethyl 5,6,7,8-tetrahydro-11-chloro-10-methoxymethyloxy-8-oxo-4H-azocino[3,2,1-hi]indole-2-carboxylate.

Workup

  1. filtrationThe insoluble material was filtered off
  2. additionthe filtrate was poured into ice water
  3. extractionextracted twice with ethyl acetate
  4. washThe extract solution was washed with a 5% aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe resulting residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=2/98)

Sources & evidence

ORD record
ord-987f4abc8d7a4824bd16efda11aa4af6
Source dataset
uspto-grants-2001_08
Patent number
US06271251B1

Reaction notes

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