Pyridine → 2-[2-(2-Methoxyphenyl)ethoxy]ethyl toluene-4-sulphonate

HRID 1176288Notes

Reaction equation

HRID 1176288 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH2:10][O:11][CH2:12][CH2:13][OH:14].N1C=CC=CC=1.[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1>ClCCl.CN(C)C1C=CN=CC=1>[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27]([O:14][CH2:13][CH2:12][O:11][CH2:10][CH2:9][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])(=[O:29])=[O:28])=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 591495282-[2-(2-Methoxyphenyl)ethoxy]ethanol

Product 1

HCID 866099992-[2-(2-Methoxyphenyl)ethoxy]ethyl toluene-4-sulphonate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

The solution of 7.50 g of 2-[2-(2-methoxyphenyl)ethoxy]ethanol in 75 ml of dichloromethane is admixed successively with 8.5 ml of pyridine, 0.519 g of 4-dimethylaminopyridine and 9.10 g of p-toluenesulphonyl chloride, and stirred at room temperature over 16 hours. The reaction mixture is washed with brine (2×200 ml). The organic phase is dried with sodium sulphate, filtered and concentrated by evaporation. The title compound is obtained as a slightly yellowish oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.26 (1:2 EtOAc-heptane); Rt=5.02.

Workup

  1. washThe reaction mixture is washed with brine (2×200 ml)
  2. dry with materialThe organic phase is dried with sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-5cc097cb480a45abb06c739f6ec7281e
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

Loading…