4-Toluenesulfonyl chloride → 3,6,9,12,15-Pentaoxaheptadecane-1,17-diol, 1-4-methylbenzenesulfonate

HRID 78712노트

반응식

HRID 78712 반응식
[CH2:1]([OH:19])[CH2:2][O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][OH:18].[S:20](Cl)([C:23]1[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=1)(=[O:22])=[O:21]>C(Cl)Cl>[CH3:27][C:26]1[CH:28]=[CH:29][C:23]([S:20]([O:18][CH2:17][CH2:16][O:15][CH2:14][CH2:13][O:12][CH2:11][CH2:10][O:9][CH2:8][CH2:7][O:6][CH2:5][CH2:4][O:3][CH2:2][CH2:1][OH:19])(=[O:22])=[O:21])=[CH:24][CH:25]=1

참가 물질

4

반응물 2

HCID 73974-Toluenesulfonyl chlorideHCID 17472Hexaethylene Glycol

생성물 1

HCID 104331623,6,9,12,15-Pentaoxaheptadecane-1,17-diol, 1-4-methylbenzenesulfonate수율 75%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a chilled (0° C.) solution of hexaethylene glycol (5.41 g, 19.2 mmol) in DCM (191 mL) were added TsCl (4.02 g, 21.1 mmol), Ag2O (6.67 g, 28.8 mmol), and KI (0.64 g, 3.84 mmol). After stirring for 20 min the reaction mixture was filtered through a 4 cm pad of celite and flushed with EtOAc. The resulted filtrate was concentrated under reduced pressure to give a yellow oil. The crude product was purified via silica flash chromatography using 3:2 DCM/Acetone as an eluent, providing 33 (6.24 g, 75%): 1H NMR (300 MHz, CDCl3) δ 7.79 (d, J=8.2 Hz, 2H), 7.33 (d, J=8.2 Hz, 2H), 4.23-4.07 (m, 2H), 3.82-3.51 (m, 22H), 2.55 (d, J=6.0 Hz, 1H), 2.44 (s, 3H).

후처리

  1. filtrationwas filtered through a 4 cm pad of celite
  2. customflushed with EtOAc
  3. concentrationThe resulted filtrate was concentrated under reduced pressure
  4. customto give a yellow oil
  5. customThe crude product was purified via silica flash chromatography

출처 및 근거

ORD 기록
ord-3fe1ecb832314323a0f57356673c8998
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841460B2

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