p-Toluenesulfonic acid monohydrate → HCID 9835846, compound

HRID 2229858Notes

Reaction equation

HRID 2229858 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:19][CH2:20][CH2:21][O:22]C3CCCCO3)[C:16]3[C:11](=[CH:12][C:13]([C:17]#[N:18])=[CH:14][CH:15]=3)[CH2:10][O:9]2)=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([CH2:19][CH2:20][CH2:21][OH:22])[C:16]3[C:11](=[CH:12][C:13]([C:17]#[N:18])=[CH:14][CH:15]=3)[CH2:10][O:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 15520972HCID 15520972, compound

Product 1

HCID 9835846HCID 9835846, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(4-fluorophenyl)-1-[3-(tetrahydropyranyloxy)propyl]-1,3-dihydro-5-isobenzofurancarbonitrile (1.5 g, 4.1 mmol) in methanol was added catalytic amount of p-toluenesulfonic acid monohydrate (60 mg) and the resulting mixture was stirred at room temperature for 1 h and then evaporated. Silica gel chromatography (heptane, EtOAc 5:1) gave the title product (1.0 g, 91%). 1H NMR (CDCl3) was identical with that obtained from 1-[(3-benzyloxy)propyl]-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofurancarbonitrile.

Workup

  1. customevaporated

Sources & evidence

ORD record
ord-06aab0e43d8e4f5ba1f55bdcc1f2344a
Source dataset
uspto-grants-2002_07
Patent number
US06420574B1

Reaction notes

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