Tetrahydrofuran → HCID 15285720, compound

HRID 374818Notes

Reaction equation

HRID 374818 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

49 mg of sodium hydride is added to a THF solution of 0.2 mL of pyrrolidine, and this mixture is agitated for one hour at room temperature. To this is added 54 mg of (6-methoxy-2-cyclohexylbenzo[b]thien-3-yl)[4-(2 -chloroethoxy)phenyl]methanone, and this mixture is heated and refluxed for ten hours. Water is added and extracted with ethyl acetate, and this extract is refined by TLC (developing solvent was chloroform:methanol=19:1), which gives 12 mg of (6-methoxy-2-cyclohexylbenzo[b]thien-3-yl)[4-[2-(1-pyrrolidinyl)ethoxy)phenyl]methanone.

Workup

  1. temperaturethis mixture is heated
  2. temperaturerefluxed for ten hours
  3. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-45c47faf695a47a7959383f08931d471
Source dataset
uspto-grants-1996_01
Patent number
US05482950

Reaction notes

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