Pyridine → HCID 13138782, compound

HRID 1864013Notes

Reaction equation

HRID 1864013 reaction equation
[CH:1]1([OH:8])[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3][CH2:2]1.N1C=CC=CC=1.[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1>C(Cl)(Cl)Cl>[OH:7][CH:4]1[CH2:5][CH2:6][CH:1]([O:8][S:21]([C:18]2[CH:19]=[CH:20][C:15]([CH3:25])=[CH:16][CH:17]=2)(=[O:23])=[O:22])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 111621,4-Cyclohexanediol

Product 1

HCID 13138782HCID 13138782, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

step 1—To a solution of 1,4-cyclohexanediol (20.0 g, 172 mmol) and pyridine (100 mL) cooled to 0° C. was added dropwise over 2 h a solution of 32.0 g (168 mmol)p-toluenesulfonyl chloride in CHCl3 (100 mL). After the addition was complete the reaction mixture was stirred at RT for 17 h. The solvent was evaporated in vacuo and the residue was taken up in refluxing toluene and petroleum ether was added until the solution became cloudy. The mixture was cooled and the supernatant was decanted. The remaining solid was dissolved in DCM and vacuum filtered through a pad of SiO2. The filter cake was washed with a mixture of DCM/MeOH (95:5). The dark golden oil was dried under vacuum to afford 35.6 g (78%) of toluene-4-sulfonic acid 4-hydroxy-cyclohexyl ester (76) contaminated with a small amount of bis-tosylate: 1H NMR (CDCl3, 300 MHz): δ 7.79 (dd, 2H), 7.73 (dd, 2H), 4.64-4.48 (m, 1H), 3.75-3.69 (m, 1H), 2.45 (s, 3H), 1.95-1.83 (m, 3H), 1.70-1.26 (m, 6H).

Workup

  1. additionAfter the addition
  2. customThe solvent was evaporated in vacuo
  3. temperaturein refluxing toluene and petroleum ether
  4. additionwas added until the solution
  5. temperatureThe mixture was cooled
  6. customthe supernatant was decanted
  7. dissolutionThe remaining solid was dissolved in DCM
  8. filtrationvacuum filtered through a pad of SiO2
  9. washThe filter cake was washed with a mixture of DCM/MeOH (95:5)
  10. customThe dark golden oil was dried under vacuum

Sources & evidence

ORD record
ord-bad0901390764eab98e6301778f72c7f
Source dataset
uspto-grants-2009_12
Patent number
US07625891B2

Reaction notes

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