1,3-Butadienyl acetate → HCID 56987068, compound

HRID 1598416Notes

Reaction equation

HRID 1598416 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 resulting 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 resulting adduct was dissolved in 10 mL of toluene
  3. customEvaporation of the solvents

Sources & evidence

ORD record
ord-3c117aeeebfb40ab946cdf592b7d784d
Source dataset
uspto-grants-1998_04
Patent number
US05736523

Reaction notes

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