tert-Butyl hydroperoxide → (trans)-3-(7-Phenyl-1,2-heptadiene-4,6-diynyl)oxiranemethanol

HRID 280395

Reaction equation

HRID 280395 reaction equation
[C:1]1([C:7]#[C:8][C:9]#[C:10][CH:11]=[C:12]=[CH:13][CH:14]=[CH:15][CH2:16][OH:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O:22]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][CH:11]=[C:12]=[CH:13][C@@H:14]2[O:22][C@H:15]2[CH2:16][OH:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 6410tert-Butyl hydroperoxideHCID 5394307710-Phenyl-7,9-decadiyne-2,4,5-trien-1-ol

Product 1

HCID 86740795(trans)-3-(7-Phenyl-1,2-heptadiene-4,6-diynyl)oxiranemethanol

Reagents, catalysts & solvents 2

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

Procedure

To a stirred solution of 20 mg (0.090 mmole) of 10-phenyl-7,9-decadiyne-2,4,5-trien-1-ol in 4 ml of benzene was added 2 mg of vanadyl acetylacetonate and 50 μl (0.26 mmole) of a 5.43M solution of t-butyl hydroperoxide in benzene. The mixture was stirred for two hours. The mixture was concentrated and the residue was purified via flash chromatography to afford 7 mg of the title compound as an approximately 1:1 mixture of diastereomers.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified via flash chromatography

Sources & evidence

ORD record
ord-20964b5dd03d42a3966e05f64e1c7cd4
Source dataset
uspto-grants-1986_05
Patent number
US04588828

Linked notes

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