4-Toluenesulfonyl chloride → PEG6-Tos

HRID 78709

반응식

HRID 78709 반응식
[CH2:1]([OH:16])[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][OH:15].[S:17](Cl)([C:20]1[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=1)(=[O:19])=[O:18]>C(Cl)Cl>[CH3:24][C:23]1[CH:25]=[CH:26][C:20]([S:17]([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:16])(=[O:19])=[O:18])=[CH:21][CH:22]=1

참가 물질

4

반응물 2

HCID 73974-Toluenesulfonyl chlorideHCID 62551Pentaethylene glycol

생성물 1

HCID 15198040PEG6-Tos수율 75.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a chilled (0° C.) solution of pentaethylene glycol (2.13 g, 8.92 mmol) in DCM (89 mL) were added TsCl (1.87 g, 9.81 mmol), Ag2O (3.10 g, 0.134 mmol), and KI (0.296 g, 1.78 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 26 (2.63 g, 75%): 1H NMR (300 MHz, CDCl3) δ 7.80 (d, J=8.2 Hz, 2H), 7.34 (d, J=8.2 Hz, 2H), 4.20-4.11 (m, 2H), 3.76-3.54 (m, 18H), 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-12ee9a1fc4cc4e2985547d2afbf4174a
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841460B2

연결된 노트

불러오는 중…