Pyridine → [1-(Hydroxymethyl)-4-methylidenecyclohexyl]methyl 4-methylbenzenesulfonate

HRID 2040897Notes

Reaction equation

HRID 2040897 reaction equation
[OH:1][CH2:2][C:3]1([CH2:10][OH:11])[CH2:8][CH2:7][C:6](=[CH2:9])[CH2:5][CH2:4]1.N1C=CC=CC=1.[C:18]1([CH3:28])[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1>ClCCl>[CH3:28][C:18]1[CH:23]=[CH:22][C:21]([S:24]([O:1][CH2:2][C:3]2([CH2:10][OH:11])[CH2:8][CH2:7][C:6](=[CH2:9])[CH2:5][CH2:4]2)(=[O:26])=[O:25])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 66603642[1-(Hydroxymethyl)-4-methylene-cyclohexyl]methanol

Product 1

HCID 86662878[1-(Hydroxymethyl)-4-methylidenecyclohexyl]methyl 4-methylbenzenesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of Compound 100b (0.25 g, 1.6 mmol) and pyridine (0.40 mL) in dichloromethane was added at 0° C. a solution of para-toluenesulphonyl chloride (0.336 g, 1.76 mmol) in 1 mL of dichloromethane. The reaction mixture was stirred at 0° C. for 30 min., then at r.t. for 3.5 h. Dilution with dichloromethane, washing with 1M aqueous NaHSO4 and brine, drying with Na2SO4, afforded, after evaporation, a crude which was purified by means of automated flash chromatography (SP01®TM-Biotage; gradient Dichloromethane-Methanol from 1:0 to 95:5) to give the title

Workup

  1. waitat r.t. for 3.5 h
  2. washDilution with dichloromethane, washing with 1M aqueous NaHSO4 and brine
  3. dry with materialdrying with Na2SO4
  4. customafforded
  5. customafter evaporation
  6. customa crude which was purified by means of automated flash chromatography (SP01®TM-Biotage; gradient Dichloromethane-Methanol from 1:0 to 95:5)
  7. customto give the title

Sources & evidence

ORD record
ord-34873fa6358848f5b6204440f34f90c1
Source dataset
uspto-grants-2013_11
Patent number
US08580962B2

Reaction notes

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