Pyridine → 4-((1R,2S)-1-cyano-2-hexylcyclopropyl)phenyl 4-(4-octyloxyphenyl)benzoate

HRID 973519Notes

Reaction equation

HRID 973519 reaction equation
[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[C:25]([C@:27]1([C:36]2[CH:41]=[CH:40][C:39]([OH:42])=[CH:38][CH:37]=2)[CH2:29][C@@H:28]1[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])#[N:26].N1C=CC=CC=1.CCOCC>ClCCl>[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:24]=[CH:23][C:19]([C:20]([O:42][C:39]3[CH:38]=[CH:37][C:36]([C@@:27]4([C:25]#[N:26])[CH2:29][C@@H:28]4[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[CH:41][CH:40]=3)=[O:21])=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 4

HCID 1049PyridineHCID 3283Diethyl EtherHCID 110784734-(4-Octyloxyphenyl)benzoyl chlorideHCID 15733984(1R,2S)-1-cyano-2-hexyl-1-(4-hydroxyphenyl)cyclopropane

Product 1

HCID 157339864-((1R,2S)-1-cyano-2-hexylcyclopropyl)phenyl 4-(4-octyloxyphenyl)benzoateYield 36.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 8 ml of dichloromethane were dissolved 66 mg of 4-(4-octyloxyphenyl)benzoyl chloride and 36 mg of (1R,2S)-1-cyano-2-hexyl-1-(4-hydroxyphenyl)cyclopropane as obtained in Example 11. Thereto was added 0.5 ml of pyridine. The resulting mixture was stirred for 8 hours with refluxing, and then cooled. Thereafter, 50 ml of ether was added to the reaction mixture, and the resulting mixture was washed with diluted hydrochloric acid, water, and saturated sodium chloride aqueous solution, and then dried over anhydrous sodium sulfate. The solvent was removed by evaporation, and the residue was separated and purified by silica gel column chromatography (solvent: hexane/ethyl acetate=5/1). Thus, 30 mg of the desired compound was obtained as colorless crystals.

Workup

  1. customas obtained in Example 11
  2. temperaturewith refluxing
  3. temperaturecooled
  4. washthe resulting mixture was washed with diluted hydrochloric acid, water, and saturated sodium chloride aqueous solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed by evaporation
  7. customthe residue was separated
  8. custompurified by silica gel column chromatography (solvent: hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-4c48fa27c3f242178679f8a9538f3e5d
Source dataset
uspto-grants-1991_11
Patent number
US05064564

Reaction notes

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