Pyridine → 4-(4-Methoxyphenyl)butyl 4-methylbenzene-1-sulfonate

HRID 2220836Notes

Reaction equation

HRID 2220836 reaction equation
N1C=CC=CC=1.[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][OH:19])=[CH:11][CH:10]=1.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>C(Cl)(Cl)Cl>[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][O:19][S:26]([C:23]2[CH:24]=[CH:25][C:20]([CH3:30])=[CH:21][CH:22]=2)(=[O:28])=[O:27])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 976604-(4-Methoxyphenyl)butan-1-ol

Product 1

HCID 110459014-(4-Methoxyphenyl)butyl 4-methylbenzene-1-sulfonate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Pyridine (15 mL) was added dropwise to a cooled (0° C.) solution of 4-(4-methoxyphenyl)butanol (10.0 g, 0.055 mol) and p-toluenesulfonyl chloride (13.6 g, 0.072 mol) in dry chloroform (100 mL) under stirring. The reaction mixture was stirred overnight at room temperature. After this time, the reaction was quenched with 10% HCl (300 mL) and extracted with chloroform. The organic fraction was washed with saturated NaHCO3, water and dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue purified by flash chromatography (eluent: hexane, ethyl acetate=15:1) to provide 12.9 g (66%) of I as clear oil. 1H NMR (360 MHZ, CDCl3) δ 1.61 (m, 4H), 2.44 (s, 3H), 2.52 (m, 2H), 3.78 (s, 3H), 4.05 (m, 2H), 6.77 (d, J=12.5 Hz, 2H), 7.05 (d, J=12.5 Hz, 2H), 7.34 (d, J=10.5 Hz, 2H), 7.78 (d, J=10.5 Hz, 2H).

Workup

  1. stirringThe reaction mixture was stirred overnight at room temperature
  2. customAfter this time, the reaction was quenched with 10% HCl (300 mL)
  3. extractionextracted with chloroform
  4. washThe organic fraction was washed with saturated NaHCO3, water
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe residue purified by flash chromatography (eluent: hexane, ethyl acetate=15:1)
  8. customto provide 12.9 g (66%) of I as clear oil

Sources & evidence

ORD record
ord-c688471954224f788edae7e761470a2b
Source dataset
uspto-grants-2008_05
Patent number
US07368450B2

Reaction notes

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