Water → HCID 18800826, compound

HRID 849140Notes

Reaction equation

HRID 849140 reaction equation
N1([C:6]2[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]=2)CCCC1.O=C1CCCCC1[CH:19]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:20]([O:22]C)=[O:21].[OH2:31].[Li+].[OH-].[CH3:34]O>CN(C)C=O>[O:31]=[C:26]1[CH2:27][CH2:28][CH2:29][CH2:30][CH:25]1[CH:24]([C:6]1[CH:7]=[CH:8][C:9]([CH3:34])=[CH:10][CH:11]=1)[CH2:19][C:20]([OH:22])=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 707681-Pyrrolidino-1-cyclohexeneHCID 13268645HCID 13268645, compoundHCID 23717829Lithium hydroxide methanol

Product 1

HCID 18800826HCID 18800826, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-pyrrolidino-1-cyclohexene is refluxed with methyl a-(2-oxocyclohexyl)benzenepropanoate in dimethylformamide (DMF) for 24 hours and refluxing is continued for another hour after the addition of water. DMF is removed under reduced pressure and the residue is diluted with water and extracted three times with EtOAc. The combined EtOAc extracts are washed with 1N HCl and then with brine. The organic phase is dried over MgSO4 and evaporated to give crude methyl b-(2-cxocyclohexyl)-4-methylbenzenepropanoate. This material is treated with 1 N LiOH/methanol to give the title material.

Workup

  1. temperaturerefluxing
  2. waitis continued for another hour
  3. customDMF is removed under reduced pressure
  4. additionthe residue is diluted with water
  5. extractionextracted three times with EtOAc
  6. washThe combined EtOAc extracts are washed with 1N HCl
  7. dry with materialThe organic phase is dried over MgSO4
  8. customevaporated
  9. customto give crude methyl b-(2-cxocyclohexyl)-4-methylbenzenepropanoate

Sources & evidence

ORD record
ord-65f23ca2dfcd4464b30fa58930cbe4ac
Source dataset
uspto-grants-2000_01
Patent number
US06011028

Reaction notes

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