Ammonium Chloride → Methyl 2-oxo-5-(pyridin-4-yl)cyclohexane-1-carboxylate

HRID 728315Notes

Reaction equation

HRID 728315 reaction equation
CC(C)([O-])C.[K+].[CH3:7][O:8][C:9](=[O:24])[CH2:10][CH2:11][CH:12]([C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1)[CH2:13][CH2:14][C:15]([OH:17])=O.[Cl-].[NH4+]>O1CCCC1>[CH3:7][O:8][C:9]([CH:10]1[CH2:11][CH:12]([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)[CH2:13][CH2:14][C:15]1=[O:17])=[O:24]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxideHCID 53880921HCID 53880921, compound

Product 1

HCID 13986053Methyl 2-oxo-5-(pyridin-4-yl)cyclohexane-1-carboxylateYield 39.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 100 ml of tetrahydrofuran, there was added 13 g of potassium t-butoxide. A solution of 26 g of 4-(4-pyridyl)pimelic acid methyl ester in 50 ml of tetrahydrofuran was added at 20° to 40° C. and the mixture was stirred for 2 hours. After the reaction was completed, the mixture was treated with saturated aqueous solution of ammonium chloride and then extracted with ether. The ether solution was washed with water and dried. Ether was distilled off and the residue was recrystallized from ether. There was obtained 9.6 g of 2-methoxycarbonyl-4-(4-pyridyl)cyclohexanone: m.p. 82°-83° C.

Workup

  1. extractionextracted with ether
  2. washThe ether solution was washed with water
  3. customdried
  4. distillationEther was distilled off
  5. customthe residue was recrystallized from ether

Sources & evidence

ORD record
ord-544212aabfe7409a911fa91d30ca9b96
Source dataset
uspto-grants-1991_09
Patent number
US05047545

Reaction notes

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