Cyclohexanol → HCID 62936067, compound

HRID 1983570Notes

Reaction equation

HRID 1983570 reaction equation
[CH:1]1([OH:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Cl[C:11]1[CH:16]=[C:15](C#N)[CH:14]=[CH:13][N:12]=1.[CH3:19][N:20]1CCCC1=O>O>[CH:1]1([O:7][C:15]2[CH:14]=[CH:13][N:12]=[C:11]([C:19]#[N:20])[CH:16]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 7966CyclohexanolHCID 13387N-methyl-2-pyrrolidoneHCID 24758Sodium hydrideHCID 5686382-Chloro-4-cyanopyridine

Product 1

HCID 62936067HCID 62936067, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of cyclohexanol (2.84 g, 3.00 mL, 2.84 mmol) in 1-methyl-2-pyrrolidinone (20 mL) was added sodium hydride (1.19 g of 60% dispersion, 29.8 mmol) in small portions over 5 minutes. After stirring for an additional 5 minutes, 2-chloro-4-cyanopyridine (3.75 g, 27.0 mmol) was added and the resulting red-brown solution was heated at 100° C. for 10 minutes. The reaction mixture then was poured onto ice. The mixture was diluted with water and extracted with ether. The combined organic phases were washed with water and brine, dried (magnesium sulfate) and concentrated to provide a yellow oil. Flash chromatography over silica (hexanes/ethyl acetate) afforded 4.17 g (76%) of the desired product as a cloudy oil which solidified on standing: 1H NMR (CDCl3) δ 8.44 (d, J=5.8 Hz, 1H), 7.17 (d, J=2.4 Hz, 1H), 6.95 (dd, J=2.4, 5.8 Hz, 1H), 4.40-4.33 (m, 1H), 1.98-1.95 (m, 2H), 1.82-1.79 (m, 2H), 1.60-1.52 (m, 3H), 1.45-1.32 (m, 3H) ppm. 13C NMR (CDCl3) δ 164.3, 152.2, 135.0, 117.3, 116.4, 113.9, 76.4, 31.1, 25.2, 23.4 ppm.

Workup

  1. additionThe reaction mixture then was poured onto ice
  2. extractionextracted with ether
  3. washThe combined organic phases were washed with water and brine
  4. dry with materialdried (magnesium sulfate)
  5. concentrationconcentrated
  6. customto provide a yellow oil

Sources & evidence

ORD record
ord-cae1d55f42e240be8cc41e2755b73875
Source dataset
uspto-grants-2009_06
Patent number
US07541466B2

Reaction notes

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