Dimethylformamide → HCID 19917189, compound

HRID 1756199Notes

Reaction equation

HRID 1756199 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-fb9b25e377ad4e59aa21e5913493ca4e
Source dataset
uspto-grants-1995_08
Patent number
US05439937

Reaction notes

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