p-Toluenesulfonic acid monohydrate → N-(2-Butyl-1-benzofuran-5-yl)acetamide

HRID 971079Notes

Reaction equation

HRID 971079 reaction equation
[CH2:1]([CH:5]1[CH:9](O)[C:8]2[CH:11]=[C:12]([NH:15][C:16](=[O:18])[CH3:17])[CH:13]=[CH:14][C:7]=2[O:6]1)[CH2:2][CH2:3][CH3:4].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCl>[CH2:1]([C:5]1[O:6][C:7]2[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:18])[CH3:17])=[CH:11][C:8]=2[CH:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 9834788N-(2-butyl-3-hydroxy-2,3-dihydro-5-benzofuranyl)acetamide

Product 1

HCID 9899437N-(2-Butyl-1-benzofuran-5-yl)acetamideYield 91.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of N-(2-butyl-3-hydroxy-2,3-dihydro-5-benzofuranyl)acetamide [9a] (2.50 g, 10.0 mmol), p-toluenesulfonic acid monohydrate (0.19 g, 1.0 mmol) and dichloromethane (30 mL) was stirred for 1 hour at room temperature and passed through short silica gel column. The column was washed with dichloromethane (300 mL). The solvent was evaporated under reduced pressure to give 2.11 g (91.3%) of N-(2-butyl-5-benzofuranyl)acetamide [10a] as off-white crystals with mp 71-73° C.

Workup

  1. washThe column was washed with dichloromethane (300 mL)
  2. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-c762448f1e8a400f953fa2d75042c6cb
Source dataset
uspto-grants-2007_12
Patent number
US07312345B2

Reaction notes

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