Pyridine → 2-(2-(2-Methoxyethoxy)ethoxy)ethyl 4-methylbenzenesulfonate

HRID 861665Notes

Reaction equation

HRID 861665 reaction equation
[C:1]1(C)[C:2]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.[CH3:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][OH:22].N1C=CC=C[CH:24]=1>>[CH2:21]([O:22][S:7]([C:2]1[CH:1]=[CH:6][C:5]([CH3:24])=[CH:4][CH:3]=1)(=[O:8])=[O:9])[CH2:20][O:19][CH2:18][CH2:17][O:16][CH2:15][CH2:14][O:13][CH3:12]

Participants

4

Reactant 3

HCID 1049PyridineHCID 8178Triethylene glycol monomethyl etherHCID 8623o-Toluenesulfonyl chloride

Product 1

HCID 99488982-(2-(2-Methoxyethoxy)ethoxy)ethyl 4-methylbenzenesulfonate

Procedure

Toluenesulfonyl chloride (7.15 g, 37.5 mmol) was added to a solution of triethyleneglycol monomethyl ether (5.0 ml, 5.13 g, 31.2 mmol) in 100 ml pyridine. The solution was stirred at RT overnight, the solvent removed and the residue extracted twice with CH2Cl2, washed with 0.1N HCl, water, NaHCO3, brine, dried with MgSO4 and evaporated. 4.5 g crude product was obtained (45%). 1H NMR: (CDCl3, 200 MHz) d 7.80 (d, 2H, ArH), 7.33 (d, 2H, ArH), 4.15 (t, 2H, TsOCH2), 3.80-3.45 (m, 10H, OCH3), 3.36 (d, 3H, OCH3), 2.44 (s, 3H, ArCH3).

Workup

  1. customthe solvent removed
  2. extractionthe residue extracted twice with CH2Cl2
  3. washwashed with 0.1N HCl, water, NaHCO3, brine
  4. dry with materialdried with MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-f290c4cc24224df4ab45e2b5669c9dfa
Source dataset
uspto-grants-1998_02
Patent number
US05714606

Reaction notes

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