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

HRID 276802

반응식

HRID 276802 반응식
[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>>[S:7]([O:22][CH2:21][CH2:20][O:19][CH2:18][CH2:17][O:16][CH2:15][CH2:14][O:13][CH3:12])([C:2]1[CH:1]=[CH:6][C:5]([CH3:24])=[CH:4][CH:3]=1)(=[O:8])=[O:9]

참가 물질

4

반응물 3

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

생성물 1

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

실험 절차

A solution of toluene sulfonyl chloride (Aldrich, 38 g) and triethylene glycol monomethyl ether (Aldrich, 16.4 g) in dry pyridine (150 ml) was stirred at 0° C. (icebath) for 4 h, followed by 18 h at ambient temperature. The solution was then poured onto ice water (500 ml) and extracted with diethyl ether (3×300 ml). The ether extracts were combined, washed with hydrochloric acid (3 N) and water, dried (sodium sulfate), and concentrated to provide triethylene glycol methyl tosyl ether as a colorless oil (20.0 g, 62% based on glycol), 1H-NMR (CDCl3) δ: 7.75 (d, J=8.0 Hz, 2, 2 phenyl CH), 7.30 (d, J=8.1 Hz, 2, 2 phenyl CH), 4.11 (t, J=4.8 Hz, 2, CH2OS), 3.65-3.41 (m, 10, 5 CH2O), 3.32 (s, 3, CH3O ) and 2.40 (s, 3, benzylic CH3).

후처리

  1. additionThe solution was then poured onto ice water (500 ml)
  2. extractionextracted with diethyl ether (3×300 ml)
  3. washwashed with hydrochloric acid (3 N) and water
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c63b83dc42b8487997df55e2e2303e62
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06355646B1

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