Tetrahydrofuran → HCID 15285720, compound

HRID 2259214Notes

Reaction equation

HRID 2259214 reaction equation
[H-].[Na+].C1COCC1.[NH:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1.[CH3:13][O:14][C:15]1[CH:16]=[CH:17][C:18]2[C:22]([C:23]([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33]Cl)=[CH:27][CH:26]=3)=[O:24])=[C:21]([CH:35]3[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]3)[S:20][C:19]=2[CH:41]=1>O>[CH3:13][O:14][C:15]1[CH:16]=[CH:17][C:18]2[C:22]([C:23]([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][N:8]4[CH2:12][CH2:11][CH2:10][CH2:9]4)=[CH:27][CH:26]=3)=[O:24])=[C:21]([CH:35]3[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]3)[S:20][C:19]=2[CH:41]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 31268PyrrolidineHCID 15285719HCID 15285719, compound

Product 1

HCID 15285720HCID 15285720, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

48 mg of sodium hydride was added to a THF solution of 0.2 ml of pyrrolidine, followed by stirring at room temperature for 1 hour. 54 mg of (6-methoxy-2-cyclohexylbenzo[b]thien-3-yl)[4-(2-chloroethoxy)phenyl]methanone was added, followed by reflux with heating for 10 hours. Water was added, the mixture was extracted with ethyl acetate, and the extract was purified by TLC (developing solvent, chloroform:methanol=9:1) to obtain 12 mg of (6-methoxy-2-cyclohexylbenzo[b]thien-3-yl)[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]methanone.

Workup

  1. temperatureby reflux
  2. temperaturewith heating for 10 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. customthe extract was purified by TLC (developing solvent, chloroform:methanol=9:1)

Sources & evidence

ORD record
ord-7c6a9850ddaa4e3493d853484b568020
Source dataset
uspto-grants-1995_12
Patent number
US05472962

Reaction notes

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