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

HRID 25125Notes

Reaction equation

HRID 25125 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-sulfonateYield 70.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Pyridine (15 mL) was added drop wise 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 1 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, 2H), 7.05 (d, 2H), 7.34 (d, 2H), 7.78 (d, 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)

Sources & evidence

ORD record
ord-a58961e48bd74daebc9cb4543b0c51f4
Source dataset
uspto-grants-2005_02
Patent number
US06858615B2

Reaction notes

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