Dimethylformamide → HCID 23362215, compound

HRID 1082126Notes

Reaction equation

HRID 1082126 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16](Cl)[C:17]([O:19][CH3:20])=[O:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22]1([S:28]([O-:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[Na+].CN(C)C=O>O>[C:22]1([S:28]([CH:16]([CH2:15][C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:10][CH:11]=2)[C:17]([O:19][CH3:20])=[O:18])(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 2723840Benzenesulfinic acid, sodium saltHCID 10780869Methyl 3-(4-benzyloxyphenyl)-2-chloropropanoate

Product 1

HCID 23362215HCID 23362215, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl 3-(4-benzyloxyphenyl)-2-chloropropanoate (International Patent Appl., Publication No. WO 9101337) (0.50 g), sodium benzenesulphinate (0.29 g) and dry N,N-dimethylformamide (25 mL) was heated at 80° C. for 24 hrs. The mixture was cooled and diluted with water (500 mL), then extracted with dichloromethane (2×250 mL). The combined organic solutions were washed with water (2×250 mL) and brine (250 mL), dried (MgSO4) and evaporated. The residue was chromatographed on silica gel with dichloromethane as eluent to afford the title compound.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with dichloromethane (2×250 mL)
  3. washThe combined organic solutions were washed with water (2×250 mL) and brine (250 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was chromatographed on silica gel with dichloromethane as eluent

Sources & evidence

ORD record
ord-f8d99f315e7c4837bf0a63ef6c8feb74
Source dataset
uspto-grants-1996_12
Patent number
US05589492

Reaction notes

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