trans-2-Methylcyclopentan-1-ol → HCID 131735830, compound

HRID 2206072Notes

Reaction equation

HRID 2206072 reaction equation
[Br:1][C:2]1[CH:3]=[C:4](/[CH:7]=[CH:8]/[C:9]([O:11][CH2:12][CH3:13])=[O:10])[NH:5][CH:6]=1.[CH3:14][C@@H:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1O.C(P(CCCC)(CCCC)=CC#N)CCC>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4](/[CH:7]=[CH:8]/[C:9]([O:11][CH2:12][CH3:13])=[O:10])[N:5]([C@@H:16]2[CH2:17][CH2:18][CH2:19][C@@H:15]2[CH3:14])[CH:6]=1

Participants

5

Reactant 3

HCID 32804trans-2-Methylcyclopentan-1-olHCID 4622928CyanomethylenetributylphosphoraneHCID 131735828HCID 131735828, compound

Product 1

HCID 131735830HCID 131735830, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of ethyl (2E)-3-(4-bromo-1H-pyrrol-2-yl)acrylate (1.3 g), trans-2-methylcyclopentanol (0.64 g) and 2-(tributylphosphoranylidene)acetonitrile (1.928 g) in toluene (12.6 mL) was stirred with heating under reflux for 22 hr under argon atmosphere. The reaction mixture was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (608 mg).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 22 hr under argon atmosphere
  3. customThe reaction mixture was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-4eee57bcbf6c401ba5e0171104f571de
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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