tert-Butyl hydroperoxide → (trans)-3-(6-Phenyl-1,3,5-hexatriynyl)oxiranemethanol

HRID 280397Notes

Reaction equation

HRID 280397 reaction equation
[C:1]1([C:7]#[C:8][C:9]#[C:10][C:11]#[C:12]/[CH:13]=[CH:14]/[CH2:15][OH:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O:21]O)(C)(C)C>C1C=CC=CC=1.C/C(/O)=C\C(C)=O.C/C(/O)=C\C(C)=O.O=[V]>[C:1]1([C:7]#[C:8][C:9]#[C:10][C:11]#[C:12][C@@H:13]2[O:21][C@H:14]2[CH2:15][OH:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 6410tert-Butyl hydroperoxide2×HCID 13632676(E)-9-phenyl-2-nonen-4,6,8-triyn-1-ol

Product 1

HCID 86740798(trans)-3-(6-Phenyl-1,3,5-hexatriynyl)oxiranemethanol

Reagents, catalysts & solvents 2

HCID 16217092Bis(2,4-pentanedionato)vanadium(IV) OxideCatalystHCID 241BenzeneSolvent2×

Procedure

To a stirred solution of 103 mg (0.50 mmole) of (E)-9-phenyl-2-nonen-4,6,8-triyn-1-ol in 20 ml of dry benzene was added 5 mg of vanadyl acetylacetonate and 0.095 ml (0.50 mmole) of a 5.24M solution of t-butylhydroperoxide in benzene. Further 0.095 ml potions of t-butyl hydroperoxide solution were added after 2 hours and 31/2 hours. After stirring for 18 hours, the benzene solution was concentrated and purified via preparative thin layer chromatography (Analtech, 2 mm, silica gel; ether-hexane 1:1) to afford 59 mg of the title compound, melting point 68°-70° C.

Workup

  1. custom2 hours
  2. concentrationthe benzene solution was concentrated
  3. custompurified via preparative thin layer chromatography (Analtech, 2 mm, silica gel; ether-hexane 1:1)

Sources & evidence

ORD record
ord-a3c9198c6f0e4a96b3cccdf47ca6afb2
Source dataset
uspto-grants-1986_05
Patent number
US04588828

Reaction notes

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