p-Toluenesulfonic acid monohydrate → 4-[2-(2-Oxoethyl)-2,3-dihydro-1-benzofuran-5-yl]benzonitrile

HRID 494815Notes

Reaction equation

HRID 494815 reaction equation
C[O:2]/[CH:3]=[CH:4]/[CH:5]1[CH2:9][C:8]2[CH:10]=[C:11]([C:14]3[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=3)[CH:12]=[CH:13][C:7]=2[O:6]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O.C(Cl)Cl>[O:2]=[CH:3][CH2:4][CH:5]1[CH2:9][C:8]2[CH:10]=[C:11]([C:14]3[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=3)[CH:12]=[CH:13][C:7]=2[O:6]1

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 222746034-{2-[(e)-2-Methoxyethenyl]-2,3-dihydro-1-benzofuran-5-yl}benzonitrile

Product 1

HCID 222744344-[2-(2-Oxoethyl)-2,3-dihydro-1-benzofuran-5-yl]benzonitrileYield 87%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of Example 67A (0.5 g, 1.8 mmol) in acetone (10 mL) and p-toluenesulfonic acid monohydrate (0.51 g, 2.7 mmol) was stirred for 45 minutes, diluted with CH2Cl2 (150 mL), washed with cold aqueous sodium bicarbonate (2×100 mL, 10% solution), water (2×100 mL), dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified on silica using CH2Cl2 to give the titled compound (0.41 g, 87%). 1HNMR (CDCl3): 2.95 (m, 2H), 3.65 (m, 3H), 6.82 (d, J=7 Hz, 1H), 7.40 (m, 2H), 7.62 (m, 4H), 9.55 (d, J=7 Hz, 1H); MS (DCI) 263 (M+), 281 (M+NH4+).

Workup

  1. washwashed with cold aqueous sodium bicarbonate (2×100 mL, 10% solution), water (2×100 mL)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified on silica

Sources & evidence

ORD record
ord-49fd57e90bce4e198f86be88b69e2d7b
Source dataset
uspto-grants-2009_05
Patent number
US07538138B2

Reaction notes

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