4-tert-Butylcyclohexanol → HCID 12602932, compound

HRID 1485838Notes

Reaction equation

HRID 1485838 reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([OH:11])[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[S:12](Cl)([C:15]1[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=1)(=[O:14])=[O:13]>N1C=CC=CC=1>[CH3:19][C:18]1[CH:20]=[CH:21][C:15]([S:12]([O:11][CH:8]2[CH2:7][CH2:6][CH:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH2:10][CH2:9]2)(=[O:14])=[O:13])=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 73914-tert-ButylcyclohexanolHCID 73974-Toluenesulfonyl chloride

Product 1

HCID 12602932HCID 12602932, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-(tert-butyl)cyclohexan-1-ol (500 mg, 3 mmol) was dissolved in pyridine (50 mL) and stirred at room temperature for 30 min. Tosyl chloride (915 mg, 4.79 mmol) was added to the reaction mixture and allowed to stir overnight. The reaction was quenched by addition of water (50 mL) and extracted with ether. (3×20 mL) washed with saturated CuSO4, water, saturated aqueous NaHCO3, water, and dried, (Na2SO4) concentrated and purified (10% EtOAc in hexane) to give 38 as a white solid.

Workup

  1. stirringto stir overnight
  2. customThe reaction was quenched by addition of water (50 mL)
  3. extractionextracted with ether
  4. wash(3×20 mL) washed with saturated CuSO4, water, saturated aqueous NaHCO3, water
  5. customdried
  6. concentration(Na2SO4) concentrated
  7. custompurified (10% EtOAc in hexane)

Sources & evidence

ORD record
ord-bb377f9db512446eb1ca4698c1f533e5
Source dataset
uspto-grants-2016_08
Patent number
US09422320B2

Reaction notes

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