4-Toluenesulfonyl chloride → HCID 14548032, compound

HRID 899424Notes

Reaction equation

HRID 899424 reaction equation
[C:1]1([CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][OH:26])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:27]1([CH3:37])[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1.C(N(CC)CC)C>ClCCl>[CH3:37][C:27]1[CH:32]=[CH:31][C:30]([S:33]([O:26][CH2:25][CH2:24][O:23][CH2:22][CH2:21][O:20][CH2:19][CH2:18][O:17][CH2:16][CH2:15][O:14][CH2:13][CH2:12][O:11][CH2:10][CH2:9][O:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:35])=[O:34])=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 11164646Hexaethylene Glycol Monobenzyl Ether

Product 1

HCID 14548032HCID 14548032, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

To a stirred solution of the product of step (a) (1 g) in dichloromethane (20 ml), p-toluenesulfonyl chloride (0.66 g) and triethylamine (0.5 ml) were added and the reaction was stirred at 20° C. for 24 hours. The reaction mixture was diluted with dichloromethane (100 ml) and washed with water (100 ml), brine (100 ml), dried and the solvent removed in vacuo. Purification by column chromatography on silica gel (Biotage) eluting with 10% ethyl acetate in cyclohexane gave the title compound (1 g).

Workup

  1. washwashed with water (100 ml), brine (100 ml)
  2. customdried
  3. customthe solvent removed in vacuo
  4. customPurification by column chromatography on silica gel (Biotage)
  5. washeluting with 10% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-724dfb1b09874f8297a18a5c15998304
Source dataset
uspto-grants-2008_04
Patent number
US07354966B2

Reaction notes

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