1,3-Butadienyl acetate → HCID 56987068, compound

HRID 1452392Notes

Reaction equation

HRID 1452392 reaction equation
C[O:2][CH:3]1[CH:8]2[C:9](=[O:14])[CH:10]=[CH:11][C:12](=[O:13])[CH:7]2[CH2:6][CH:5]([C:15]([CH3:17])=[O:16])[O:4]1.C(O[CH:22]=[CH:23][CH:24]=[CH2:25])(=O)C>C1C=CC=CC=1>[OH:2][CH:3]1[C:8]2[C:9](=[O:14])[C:10]3[C:11]([C:12](=[O:13])[C:7]=2[CH2:6][CH:5]([C:15]([CH3:17])=[O:16])[O:4]1)=[CH:25][CH:24]=[CH:23][CH:22]=3

Participants

4

Reactant 2

HCID 151951,3-Butadienyl acetateHCID 86750392HCID 86750392, compound

Product 1

HCID 56987068HCID 56987068, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of methyl (1-methoxy-5,8 dioxo-tetrahydrobenzo [2,3-C] pyran-3-yl) ketone (100 mg, 0.450 mmol) and acetoxy butadiene (80 μg, 0.675 mmol) in dry benzene (5 mL) was heated for 3 hours at 60° C. under argon atmosphere. The solvent was then removed in vacuo and the resultting adduct was dissolved in 10 mL of toluene and then aromatized on silica gel by flash chromatography (toluene:ethyl acetate; 90%:10% followed by 70%:30%). Evaporation of the solvents gave 37 mg (31% yield) of pure titled compound.

Workup

  1. customThe solvent was then removed in vacuo
  2. dissolutionthe resultting adduct was dissolved in 10 mL of toluene
  3. customEvaporation of the solvents

Sources & evidence

ORD record
ord-88289df42f42428e88cf9d01cfdf6683
Source dataset
uspto-grants-1997_02
Patent number
US05606037

Reaction notes

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