Hydrochloric Acid → HCID 11474906, compound

HRID 1791024Notes

Reaction equation

HRID 1791024 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][CH2:8][C:9]([CH2:11]Cl)=[CH2:10].[OH:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](=[O:22])C)=[CH:16][C:15]=1[CH2:23][S:24]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=[O:26])=[O:25].Cl.CN(C)[CH:36]=[O:37]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CCOCC.O>[Cl:7][CH2:8][C:9](=[CH2:10])[CH2:11][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([O:37][CH3:36])=[O:22])=[CH:16][C:15]=1[CH2:23][S:24]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=[O:26])=[O:25]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 158593-Chloro-2-chloromethyl-1-propeneHCID 11277725HCID 11277725, compound

Product 1

HCID 11474906HCID 11474906, compoundYield 50%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

3 g (8.62 mmol) of tetrabutylammonium iodide, 3.02 g (20.4 mmol) of potassium carbonate and then 2.36 ml (20.4 mmol) of 2-chloromethyl-3-chloro-1-propene are successively introduced into a solution of 2.5 g (8.16 mmol) of readily accessible 1-{4-hydroxy-3-[(phenylsulfonyl)methyl]phenyl}ethanone in 150 ml of N,N-dimethylformamide. The solution is stirred at ambient temperature for 20 hours and then water, ether and 1N hydrochloric acid are added, the reaction medium being cooled to 0° C. using a water bath and ice. The solid obtained by filtration is discarded, the phases are separated by settling and then the aqueous phase is extracted several times with ether. The combined organic phases are washed several times with an aqueous solution and then with brine. After drying and concentration under vacuum, the crude reaction product is purified by chromatography on silica gel (ethyl acetate/heptane 40/60) to provide 1.63 g (50%) of methyl 4-{[2-(chloromethyl)-2-propenyl]oxy}-3-[(phenyl-sulfonyl)methyl]benzoate in the form of a white solid; M.p.=92–93° C. (M.p. denotes the melting point of the compounds).

Workup

  1. temperaturethe reaction medium being cooled to 0° C.
  2. customThe solid obtained by filtration
  3. customthe phases are separated
  4. extractionthe aqueous phase is extracted several times with ether
  5. washThe combined organic phases are washed several times with an aqueous solution
  6. customAfter drying
  7. concentrationconcentration under vacuum
  8. customthe crude reaction product
  9. customis purified by chromatography on silica gel (ethyl acetate/heptane 40/60)

Sources & evidence

ORD record
ord-57535bf7c107433c9e25a290b71400a3
Source dataset
uspto-grants-2006_07
Patent number
US07071340B2

Reaction notes

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