Hexafluorophosphate → 3-(2,5-dihydrofuran-3-yl)-2,5-dihydrofuran

HRID 1357311Notes

Reaction equation

HRID 1357311 reaction equation
[CH2:1]([O:4][CH2:5][C:6]#[C:7][CH2:8][O:9][CH2:10][CH:11]=C)[CH:2]=C.F[P-](F)(F)(F)(F)F>C1(C)C=CC=CC=1>[O:9]1[CH2:10][CH:11]=[C:7]([C:6]2[CH2:5][O:4][CH2:1][CH:2]=2)[CH2:8]1

Participants

4

Reactant 2

HCID 9886HexafluorophosphateHCID 10725729HCID 10725729, compound

Product 1

HCID 102194673-(2,5-dihydrofuran-3-yl)-2,5-dihydrofuranYield 86%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1,4-bis(allyloxy)-2-butyne (157 mg, 1.02 mmol) and (p-cymene)RuCl(PCy3)(═C═C═CPh2)+PF6− (22 mg) in toluene (5 mL) is stirred for 3 h under argon at 80° C. The solvent is evaporated and the residue purified by flash chromatography using diethylether/pentane (1/4) as eluent. This affords the title compound as white solid (110 mg, 86%). 1H NMR (200 MHz, CDCl3): δ=4.70 (br. S, 8H), 5.59 (s, 2H). 13C NMR (50 MHz, CDCl3): δ=74.7, 76.0, 122.5, 131.4.

Workup

  1. customThe solvent is evaporated
  2. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-a9b1cb3cfd6f44af82ae888bb45f828b
Source dataset
uspto-grants-2003_07
Patent number
US06590048B1

Reaction notes

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