Sodium Bicarbonate → (1R,2S)-1-cyano-2-hexyl-1-(4-hydroxyphenyl)cyclopropane

HRID 973514Notes

Reaction equation

HRID 973514 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]([C@:7]1([C:16]2[CH:21]=[CH:20][C:19]([O:22]C)=[CH:18][CH:17]=2)[CH2:9][C@@H:8]1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])#[N:6].C(=O)([O-])O.[Na+]>CSC.ClCCl>[C:5]([C@:7]1([C:16]2[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=2)[CH2:9][C@@H:8]1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])#[N:6]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 6451240Aluminum(III) ChlorideHCID 15733981(1R,2S)-1-cyano-2-hexyl-1-(4-methoxyphenyl)cyclopropane

Product 1

HCID 15733984(1R,2S)-1-cyano-2-hexyl-1-(4-hydroxyphenyl)cyclopropaneYield 81%

Reagents, catalysts & solvents 2

HCID 1068Dimethyl SulfideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.38 g (10.4 mmol) of aluminum chloride in 10 ml of dimethyl sulfide (Me2S) was added, with cooling with ice, a solution of 267 mg (1 mmol) of (1R,2S)-1-cyano-2-hexyl-1-(4-methoxyphenyl)cyclopropane in 10 ml of dichloromethane. This mixture was stirred with heating for 30 minutes. Saturated sodium hydrogen carbonate aqueous solution was added to the reaction mixture, and the mixture was then subjected to extraction with 250 ml of ethyl acetate. The resulting ethyl acetate solution was washed with saturated sodium chloride aqueous solution, dried with anhydrous magnesium sulfate, and then concentrated. The residue was separated and purified by column chromatography (Kieselgel 60, hexane/ethyl acetate=5/1), thereby obtaining 197 mg (yield 81%) of (1R,2S)-1-cyano-2-hexyl-1-(4-hydroxyphenyl)cyclopropane.

Workup

  1. temperaturewith cooling with ice
  2. temperaturewith heating for 30 minutes
  3. extractionthe mixture was then subjected to extraction with 250 ml of ethyl acetate
  4. washThe resulting ethyl acetate solution was washed with saturated sodium chloride aqueous solution
  5. dry with materialdried with anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was separated
  8. custompurified by column chromatography (Kieselgel 60, hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-f822ac471ffa4d819c1217a8a474be12
Source dataset
uspto-grants-1991_11
Patent number
US05064564

Reaction notes

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