Cyclohexanemethanol → Cyclohexylmethyl 2-pyridylacetate

HRID 2352575Notes

Reaction equation

HRID 2352575 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=[O:10].[CH:12]1([CH2:18]O)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.C1(N=C=NC2CCCCC2)CCCCC1>N1C=CC=CC=1>[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][CH2:18][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:10]

Participants

5

Reactant 3

HCID 7507CyclohexanemethanolHCID 10868DicyclohexylcarbodiimideHCID 853172-Pyridineacetic acid, hydrochloride (1:1)

Product 1

HCID 14477238Cyclohexylmethyl 2-pyridylacetate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 422 mg of 2-pyridylacetic acid hydrochloride and 596 μl of cyclohexylmethanol in 5 ml of dry pyridine was added 651 mg of 1,3-dicyclohexylcarbodiimide, and the mixture was stirred for 10 hours at room temperature. The precipitates were filtered off and the filtrate was evaporated under reduced pressure. The residue was dissolved in 20 ml of a 1N-hydrochloric acid, acidic solution was washed twice with 25 ml of diethyl ether. A 2N-aqueous sodium hydroxide was added to the solution to a pH of 11. A separated oil was extracted with 50 ml of dichloromethane, and the organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure to obtain 525 mg of cyclohexylmethyl 2-pyridylacetate as an oil.

Workup

  1. filtrationThe precipitates were filtered off
  2. customthe filtrate was evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in 20 ml of a 1N-hydrochloric acid, acidic solution
  4. washwas washed twice with 25 ml of diethyl ether
  5. additionA 2N-aqueous sodium hydroxide was added to the solution to a pH of 11
  6. extractionA separated oil was extracted with 50 ml of dichloromethane
  7. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-3d123d6fba2e4d219946013b5c608482
Source dataset
uspto-grants-1989_10
Patent number
US04877795

Reaction notes

Loading…