Water → HCID 86760570, compound

HRID 1592937Notes

Reaction equation

HRID 1592937 reaction equation
[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:22])[CH2:11][C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])=[CH:6][CH:5]=1.O.C(Cl)[Cl:26]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:5]=[CH:6][C:7]([C:10](=[O:22])[CH:11]([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[Cl:26])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6344DichloromethaneHCID 22262154HCID 22262154, compound

Product 1

HCID 86760570HCID 86760570, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4.0 g (12.8 mmols) of 4-benzyloxycarbonylacetyl-benzoic acid methylester, dissolved in 40 ml of toluene, are mixed with 19.2 ml of a 1 M solution of SO2Cl2 in CH2Cl2 and stirred for 30 min at RT. At 0° C., water is added and the aqueous phase is separated and extracted twice with EtOAc. The organic phases are washed twice with sat. NaHCO3 solution, H2O and brine, dried (Na2SO4) and concentrated by evaporation. Column chromatography (SiO2; hexane/EtOAc 9:1→4:1; crude product dissolved in CH2Cl2) yielded the title compound as an oil: MS: [M+1]+=347; TLC(hexane/EtOAc 4:1) Rf=0.19.

Workup

  1. customthe aqueous phase is separated
  2. extractionextracted twice with EtOAc
  3. washThe organic phases are washed twice with sat. NaHCO3 solution, H2O and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated by evaporation
  6. dissolutionColumn chromatography (SiO2; hexane/EtOAc 9:1→4:1; crude product dissolved in CH2Cl2)

Sources & evidence

ORD record
ord-97fbe7e6f8614ef5b45d1453886b356a
Source dataset
uspto-grants-2007_11
Patent number
US07294633B2

Reaction notes

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