Dimethylformamide → HCID 19917189, compound

HRID 893457Notes

Reaction equation

HRID 893457 reaction equation
[OH:1][C:2]1[C:14]([CH2:15][CH:16]=[CH2:17])=[C:13]([OH:18])[CH:12]=[CH:11][C:3]=1[C:4]([N:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5].I[CH2:20][CH2:21][CH2:22][O:23][C:24]1[CH:37]=[CH:36][C:27]2[CH2:28][CH2:29][CH:30]([C:32]([O:34][CH3:35])=[O:33])[O:31][C:26]=2[C:25]=1CCC.C(=O)([O-])[O-].[K+].[K+].[CH3:47]N(C=O)C.C(O[CH2:56][CH3:57])(=O)C>>[CH3:35][O:34][C:32]([C:30]1([CH2:47][CH2:56][CH3:57])[CH2:29][CH2:28][C:27]2[CH:36]=[CH:37][C:24]([O:23][CH2:22][CH2:21][CH2:20][O:18][C:13]3[CH:12]=[CH:11][C:3]([C:4]([N:6]4[CH2:10][CH2:9][CH2:8][CH2:7]4)=[O:5])=[C:2]([OH:1])[C:14]=3[CH2:15][CH:16]=[CH2:17])=[CH:25][C:26]=2[O:31]1)=[O:33]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 14722828HCID 14722828, compoundHCID 15341804HCID 15341804, compound

Product 1

HCID 19917189HCID 19917189, compound

Procedure

1-[2,4-Dihydroxy-3-(2-propenyl)benzoyl]pyrrolidine (260 mg, 1.05 mmol), the compound of Example 23 (440 mg, 1.05 mmol), and potassium carbonate (350 mg, 2.4 mmol) were added to about 15 to 20 ml of DMF, and the reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate and washed with water. The organic layer was dried over magnesium sulfate and concentrated under vacuum. Chromatography of the crude material on silica gel using 20% ethyl acetate/hexane as eluant gave the product.

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-63e15fedc82641f88652b200c87515a4
Source dataset
uspto-grants-1992_06
Patent number
US05124350

Reaction notes

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