Water → HCID 19599916, compound

HRID 611247Notes

Reaction equation

HRID 611247 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].[C:7]([C:15]1[CH:31]=[CH:30][C:18]([C:19]([N:21]2[CH2:26][CH2:25][C:24]3[CH:27]=CO[C:23]=3[CH2:22]2)=[O:20])=[CH:17][CH:16]=1)(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O>CN(C)C=O>[C:7]([C:15]1[CH:31]=[CH:30][C:18]([C:19]([N:21]2[CH2:26][CH2:25][C:24]3[CH:27]=[C:2]([CH:1]=[O:5])[O:3][C:23]=3[CH2:22]2)=[O:20])=[CH:17][CH:16]=1)(=[O:14])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 65578Oxalyl chlorideHCID 19599920HCID 19599920, compound

Product 1

HCID 19599916HCID 19599916, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To 30 ml of N,N-dimethylformamide, 0.20 ml (2.3 mmol) of oxalyl chloride was added at -78° C., followed by stirring at room temperature for 15 minutes. To this mixture, a solution of 0.684 g (2.064 mmol) of 6-(4-benzoylbenzoyl)-4,5,6,7-tetrahydrofuro[2,3-c]pyridine in 10 ml of N,N-dimethylformamide was added, followed by overnight stirring at room temperature. After water was added, the reaction mixture was extracted with ethyl acetate 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel flush column chromatography (hexane/ethyl acetate=1/1 to 1/3) to yield the desired product.

Workup

  1. waitfollowed by overnight
  2. stirringstirring at room temperature
  3. extractionthe reaction mixture was extracted with ethyl acetate 3 times
  4. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe resulting crude product was purified by silica gel
  7. customflush column chromatography (hexane/ethyl acetate=1/1 to 1/3)

Sources & evidence

ORD record
ord-905ff3a43e0542cf81e5f7a9410bd547
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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