Tetrahydrofuran → 5-Cyclopropyl-1,3-benzodioxole

HRID 963838Notes

Reaction equation

HRID 963838 reaction equation
FC1C=CC(Br)=C[C:3]=1[O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Mg].C(OCC(F)=C[C:24]1(C2C=CC(F)=CC=2F)[CH2:26][CH2:25]1)(=O)C.[O:36]1CCCC1>>[CH2:3]1[O:9][C:10]2[CH:11]=[CH:12][C:13]([CH:24]3[CH2:26][CH2:25]3)=[CH:14][C:15]=2[O:36]1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 5462224MagnesiumHCID 11076399Benzene, 4-bromo-1-fluoro-2-phenoxy-HCID 542493411-(3-Acetoxy-2-fluoroprop-1-enyl)-1-(2,4-difluorophenyl)cyclopropane

Product 1

HCID 162050505-Cyclopropyl-1,3-benzodioxoleYield 28%

Procedure

The method of Example 25 was repeated using a Grignard reagent, prepared from 4-fluoro-3-phenoxyphenyl bromide (0.31 g), tetrahydrofuran (2 ml) and magnesium (22 mg) and 1-(3-acetoxy-2-fluoroprop-1-enyl)-1-(2,4-difluorophenyl)cyclopropane (Example 23) (0.11 g). The residue after evaporation was purified by preparative thin layer chromatography (solvent: diethyl ether/hexane; 1:9) and then preparative high performance liquid chromatography (column: C18; solvent: methanol; flow rate: 8 ml/min) to afford 1-(2,4-difluorophenyl)-3-(4-fluoro-3-phenoxyphenyl)prop-1-enyl)-1-(3,4-methylenedioxyphenyl)-cyclopropane (40 mg, 28%).

Workup

  1. customThe residue after evaporation
  2. customwas purified by preparative thin layer chromatography (solvent: diethyl ether/hexane; 1:9)

Sources & evidence

ORD record
ord-6ce5616be0b648f6a4fbc230779e702d
Source dataset
uspto-grants-1998_06
Patent number
US05763700

Reaction notes

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