Potassium tert-butoxide → 4-(Methoxymethyl)cyclohexanecarbonitrile

HRID 573227Notes

Reaction equation

HRID 573227 reaction equation
[CH3:1][O:2][CH2:3][CH:4]1[CH2:9][CH2:8][C:7](=O)[CH2:6][CH2:5]1.C1(C)C(S([CH2:20][N+:21]#[C-])(=O)=O)=CC=CC=1.CC(C)([O-])C.[K+]>C(COC)OC.C(O)C>[CH3:1][O:2][CH2:3][CH:4]1[CH2:9][CH2:8][CH:7]([C:20]#[N:21])[CH2:6][CH2:5]1

Participants

6

Reactant 3

HCID 23665647Potassium tert-butoxideHCID 53627694Toluenesulfonylmethyl isocyanideHCID 578290164-(Methoxymethyl)cyclohexan-1-one

Product 1

HCID 671268194-(Methoxymethyl)cyclohexanecarbonitrile

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a cold (−10° C.) solution of EXAMPLE 454C (1.18 g) and toluenesulfonylmethyl isocyanide (2.268 g) in dimethoxyethane (3 mL) and absolute ethanol (0.1 mL) was added portionwise potassium tert-butoxide (2.235 g). The reaction mixture was continued to stir maintaining the temperature below 5° C. for 30 minutes, warmed to room temperature, heated at 35° C. for 30 minutes and then at room temperature for 2 hours. The reaction mixture was concentrated and the residue was dissolved in water-brine, extracted with dichloromethane. The dichloromethane layer was purified by flash chromatography, eluted with 5% ethyl acetate in dichloromethane to provide the title compound.

Workup

  1. temperaturemaintaining the temperature below 5° C. for 30 minutes
  2. temperatureheated at 35° C. for 30 minutes
  3. concentrationThe reaction mixture was concentrated
  4. dissolutionthe residue was dissolved in water-brine
  5. extractionextracted with dichloromethane
  6. customThe dichloromethane layer was purified by flash chromatography
  7. washeluted with 5% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-3be452e411fb4d058cbd88e98d69ae46
Source dataset
uspto-grants-2015_05
Patent number
US09029404B2

Reaction notes

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