p-Toluenesulfonic acid monohydrate → 7-Methoxy-2-(tetrahydrofuran-2-yl)-benzofuran

HRID 2270115Notes

Reaction equation

HRID 2270115 reaction equation
[CH3:1][O:2][C:3]1[C:11]2[O:10][C:9]([CH:12]([OH:17])[CH2:13][CH2:14][CH2:15]O)=[CH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCl>[CH3:1][O:2][C:3]1[C:11]2[O:10][C:9]([CH:12]3[CH2:13][CH2:14][CH2:15][O:17]3)=[CH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 184236471-(7-Methoxybenzofuran-2-yl)-butane-1,4-diol

Product 1

HCID 184236387-Methoxy-2-(tetrahydrofuran-2-yl)-benzofuranYield 71.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(7-methoxybenzofuran-2-yl)-butane-1,4-diol (0.88 g) was treated with p-toluenesulfonic acid monohydrate (10 mg) and 3 Å molecular sieves in dichloromethane (10 ml) at ambient temperature. After stirring for 1 hour the solvent was removed in vacuo. The residue was purified by column chromatography on silica eluting with 20% ethyl acetate in hexane to give the title compound as a yellow oil (0.58 g).

Workup

  1. customwas removed in vacuo
  2. customThe residue was purified by column chromatography on silica eluting with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-accf0f2edee64eab80e954a15102b3a9
Source dataset
uspto-grants-2001_12
Patent number
US06331556B2

Reaction notes

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