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

HRID 280401

Reaction equation

HRID 280401 reaction equation
[C:1]1([C:7]#[C:8][C:9]#[C:10][C:11]#[C:12][C@@H:13]2[O:15][C@H:14]2[CH:16]=[CH:17][CH2:18][OH:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O:24]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][CH:13]2[O:15][CH:14]2[C@@H:16]2[O:24][C@H:17]2[CH2:18][OH:19])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 6410tert-Butyl hydroperoxideHCID 86740801(trans)-3-[3-(6-Phenyl-1,3,5-hexatriynyl)oxiranyl]-2-propen-1-ol

Product 1

HCID 86740802(trans)-3-[3-(6-Phenyl-1,3,5-hexatriynyl)oxiranyl]oxiranemethanol

Reagents, catalysts & solvents 2

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

Procedure

To a stirred solution of 22 mg (0.089 mmole) of (trans)-3-[3-(6-phenyl-1,3,5-hexatriynyl)oxiranyl]-2-propen-1-ol (see Example 6) in 5 ml of dry benzene was added 2 mg of vanadyl acetylacetonate and 50 μl (0.26 mmole) of a 5.43M solution of t-butylhydroperoxide in benzene. The mixture was stirred for 4 hours. The mixture was concentrated and the residue was purified via preparative thin layer chromatography (silica gel; ethyl acetate-hexane 1:1) to afford 11 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 preparative thin layer chromatography (silica gel; ethyl acetate-hexane 1:1)

Sources & evidence

ORD record
ord-29241dd3ea734775b194b89b1cce9b9c
Source dataset
uspto-grants-1986_05
Patent number
US04588828

Linked notes

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