Dimethylformamide → HCID 18692601, compound

HRID 1871649Notes

Reaction equation

HRID 1871649 reaction equation
CN(C)C=O.[CH3:6][O:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH:17](OS(C)(=O)=O)[C:18]([O:20][CH3:21])=[O:19])=[CH:12][CH:11]=1.[C:27]1([SH:33])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(=O)([O-])[O-].[K+].[K+]>O.C(OCC)(=O)C>[CH3:6][O:7][CH2:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:16][CH:17]([S:33][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:18]([O:20][CH3:21])=[O:19])=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 18692562HCID 18692562, compound

Product 1

HCID 18692601HCID 18692601, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 15 ml of N,N-dimethylformamide containing 745 mg of methyl 3-(4-methoxymethoxyphenyl)-2-methanesulfonyloxypropionate, 310 mg of thiophenol and 390 mg of potassium carbonate was stirred at 50° C. for 0.5 hours, and ethyl acetate and water were added to the reaction mixture. Then, the ethyl acetate layer was separated and dried over anhydrous magnesium sulfate. The ethyl acetate layer was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:4) to obtain 698 mg of the desired compound as a syrup.

Workup

  1. customThen, the ethyl acetate layer was separated
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationThe ethyl acetate layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a211cddb51314853bdb3bd6430451101
Source dataset
uspto-grants-2000_08
Patent number
US06103907

Reaction notes

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