4-Toluenesulfonyl chloride → PEG6-Tos

HRID 78709

反応式

HRID 78709 の反応式
[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

参加物

4

反応物 2

HCID 73974-Toluenesulfonyl chlorideHCID 62551Pentaethylene glycol

生成物 1

HCID 15198040PEG6-Tos収率 75.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-12ee9a1fc4cc4e2985547d2afbf4174a
出典データセット
uspto-grants-2014_09
特許番号
US08841460B2

関連ノート

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