Toluene → HCID 10856208, compound

HRID 1357313Notes

Reaction equation

HRID 1357313 reaction equation
[CH2:1]([O:4][C:5]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([C:7]#[CH:8])[CH3:6])[CH:2]=C.F[P-](F)(F)(F)(F)F.[C:22]1(C)C=CC=CC=1>>[CH3:6][C:5]1([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:7]([CH:8]=[CH2:22])=[CH:2][CH2:1][O:4]1

Participants

4

Reactant 3

HCID 1140TolueneHCID 9886HexafluorophosphateHCID 110086362-allyloxy-2-phenylbut-3-yne

Product 1

HCID 10856208HCID 10856208, compoundYield 84%

Conditions

Temperature
80 °C

Procedure

Metathesis under Photo-chemical Irradiation. A solution of 2-allyloxy-2-phenylbut-3-yne (371 mg, 1.99 mmol) and the allenylidene complex (p-cymene)RuCl(PCy3)(═C═C═CPh2)+PF6− (44 mg, 0.0496 mmol, 2.5 mol %) in toluene (10 ml) is irradiated with UV light (Hg lamp, 300 nm) for 30 minutes at room temperature under nitrogen, then stirred for 4 hours at 80° C. without UV irradiation. The solvent is evaporated and the crude product is purified by flash chromatography using ether:pentane (1:10) as the eluent. This affords the title compound as a yellowish liquid (313 mg, 84%), the spectral data of which are identical to those reported above.

Workup

  1. customMetathesis under Photo-chemical Irradiation
  2. customThe solvent is evaporated
  3. customthe crude product is purified by flash chromatography

Sources & evidence

ORD record
ord-d326e4f13f214dc5ac968ec011ff7363
Source dataset
uspto-grants-2003_07
Patent number
US06590048B1

Reaction notes

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