Tetrahydrofuran → HCID 3397621, compound

HRID 861916Notes

Reaction equation

HRID 861916 reaction equation
O1CCCC1.[OH-].[Na+].C([N:10]1[CH2:15][CH2:14][N:13]([CH:16]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)[C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[CH2:12][CH2:11]1)=O>CO>[CH3:32][O:31][C:28]1[CH:27]=[CH:26][C:25]([CH:16]([C:17]2[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=2)[N:13]2[CH2:14][CH2:15][NH:10][CH2:11][CH2:12]2)=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 19701055HCID 19701055, compound

Product 1

HCID 3397621HCID 3397621, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

6 ml of tetrahydrofuran, 9 ml of methanol and 9 ml of 10% aqueous sodium hydroxide were added to 1.68 g of the above-mentioned compound (2) followed by stirring for 2 hours at 60° C. After concentrating the reaction solution to roughly 10 ml and saturating it with sodium chloride, the concentrate was extracted with dichloromethane (20 ml×4). After drying with anhydrous sodium sulfate, the solvent was distilled off under reduced pressure to obtain 1.48 g of the target compound. Yield: 95%

Workup

  1. concentrationAfter concentrating the reaction solution to roughly 10 ml
  2. concentrationsaturating it with sodium chloride
  3. extractionthe concentrate was extracted with dichloromethane (20 ml×4)
  4. dry with materialAfter drying with anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-3ce28f15a7654ed5a6ae97c0aa173794
Source dataset
uspto-grants-1998_02
Patent number
US05716958

Reaction notes

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