Dichloromethane → HCID 13656117, compound

HRID 746047Notes

Reaction equation

HRID 746047 reaction equation
[C:1]1([C:7]2([CH2:16][CH2:17][N:18](C)[CH3:19])[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[O:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:22]([O:24][CH2:25][C:26]([Cl:29])([Cl:28])[Cl:27])=[O:23].C([O-])([O-])=O.[K+].[K+].C(Cl)Cl>O>[C:1]1([C:7]2([CH2:16][CH2:17][N:18]([C:22]([O:24][CH2:25][C:26]([Cl:29])([Cl:28])[Cl:27])=[O:23])[CH3:19])[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[O:9][CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 870632,2,2-Trichloroethyl chloroformateHCID 13656115HCID 13656115, compound

Product 1

HCID 13656117HCID 13656117, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6.0 g (22.5 mole) of 2-(3-phenyl-2,3-dihydrobenzofuran-3-yl)-N,N-dimethylethylamine, 3.72 ml (27 mmole) beta,beta,beta-trichloroethyl chloroformate, 12.4 g (90 mmole) anhydrous K2CO3, and 100 ml anhydrous CH2Cl2 was stirred at room temperature overnight. Water was then added to dissolve the inorganics and the layers were separated. The organics were washed with water and dried over MgSO4. Filtration and evaporation gave an oil, which was chromatographed with HPLC using 80% CH2Cl2 /hexane as an eluent to give 6.4 g (66%) of an oil.

Workup

  1. dissolutionto dissolve the inorganics
  2. customthe layers were separated
  3. washThe organics were washed with water
  4. dry with materialdried over MgSO4
  5. filtrationFiltration and evaporation
  6. customgave an oil, which
  7. customwas chromatographed with HPLC

Sources & evidence

ORD record
ord-3d18f7412ceb4189886892f75a358054
Source dataset
uspto-grants-1986_07
Patent number
US04602035

Reaction notes

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