Potassium Hydroxide → HCID 58495490, compound

HRID 1190982Notes

Reaction equation

HRID 1190982 reaction equation
CC1C=CC(S([O:11][CH:12]2[CH2:17][CH2:16][CH2:15][C:14]([CH3:19])([CH3:18])[CH2:13]2)(=O)=O)=CC=1.[Cl:20][C:21]1[N:26]=[CH:25][C:24](O)=[CH:23][CH:22]=1.[OH-].[K+]>CN(C=O)C>[Cl:20][C:21]1[N:26]=[CH:25][C:24]([O:11][CH:12]2[CH2:17][CH2:16][CH2:15][C:14]([CH3:18])([CH3:19])[CH2:13]2)=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 8198212-Chloro-5-hydroxypyridineHCID 15254221HCID 15254221, compound

Product 1

HCID 58495490HCID 58495490, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Under a nitrogen atmosphere, add 3,3-dimethylcyclohexyl 4-methylbenzenesulfonate (1.2 g, 4.25 mmol), 6-chloro-pyridin-3-ol (0.5 g, 3.86 mmol) and potassium hydroxide (238 mg, 4.25 mmol) to DMF (10 mL). Heat the mixture to 60° C. and stir overnight. Add water (20 mL) and diethyl ether (20 mL) and separate the layers. Extract the aqueous layer with diethyl ether (3×20 mL). Wash the combined organic extracts with brine (20 mL), dry over Na2SO4, filter, and concentrate in vacuo. Purify by chromatography on silica gel (80 g, pre-packed cartridge) eluting with hexane/EtOAc (1:0 to 1:1 over 60 min, 80 mL/min) to obtain the desired intermediate as a white solid (728 mg, 79%). MS (APCI+) m/z: 240 (M+H)+.

Workup

  1. customAdd water (20 mL) and diethyl ether (20 mL) and separate the layers
  2. extractionExtract the aqueous layer with diethyl ether (3×20 mL)
  3. washWash the combined organic extracts with brine (20 mL)
  4. dry with materialdry over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customPurify by chromatography on silica gel (80 g, pre-packed cartridge)
  8. washeluting with hexane/EtOAc (1:0 to 1:1 over 60 min, 80 mL/min)

Sources & evidence

ORD record
ord-ef91f3a78f7440d5afad6c60bad017e7
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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