4-Toluenesulfonyl chloride → PEG6-Tos

HRID 78709

Reaction equation

HRID 78709 reaction equation
[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

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 62551Pentaethylene glycol

Product 1

HCID 15198040PEG6-TosYield 75.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-12ee9a1fc4cc4e2985547d2afbf4174a
Source dataset
uspto-grants-2014_09
Patent number
US08841460B2

Linked notes

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