Toluene → HCID 11097182, compound

HRID 1598414Notes

Reaction equation

HRID 1598414 reaction equation
[O:1]=[C:2]1[C:11]2[CH2:10][CH:9]([C:12]([CH3:14])=[O:13])[O:8][CH2:7][C:6]=2[C:5](=[O:15])[CH:4]=[CH:3]1.C(O[CH:20]=[CH:21][CH:22]=[CH2:23])(=O)C.C1(C)C=CC=CC=1.C(OCC)(=O)C>C1C=CC=CC=1>[O:1]=[C:2]1[C:11]2[CH2:10][CH:9]([C:12]([CH3:14])=[O:13])[O:8][CH2:7][C:6]=2[C:5](=[O:15])[C:4]2[C:3]1=[CH:20][CH:21]=[CH:22][CH:23]=2

Participants

6

Reactant 4

HCID 1140TolueneHCID 8857Ethyl AcetateHCID 151951,3-Butadienyl acetateHCID 11030982HCID 11030982, compound

Product 1

HCID 11097182HCID 11097182, compoundYield 55.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of methyl (5,8-dioxo-3,4,5,8-tetrahydrobenzo[2,3-C] pyran-3-yl) ketone (100 mg, 0.485 mmol) and acetoxybutadiene (75 μl, 0.630 mmol) in dry benzene (5 mL) was heated for 12 hours at 60° C. under argon atmosphere. The solvent was then removed in vacuo and the resulting adduct dried under reduced pressure. The adduct was dissolved in 10 mL of ethanol and to this solution was added 1 mL of 1% K2CO3 aqueous solution. After stirring for 2 hours at R.T., the reaction mixture was neutralized (pH=6) and extracted with CH2Cl2 (2×50 mL). The organic layer was then washed with water (3×50 mL) and dried over MgSO4. Flash chromatography (toluene:ethyl acetate; 95%:5%) of the residue gave 69 mg (55% yield) of pure titled compound. (MP: 135°-136° C.).

Workup

  1. customThe solvent was then removed in vacuo
  2. customthe resulting adduct dried under reduced pressure
  3. dissolutionThe adduct was dissolved in 10 mL of ethanol and to this solution
  4. additionwas added 1 mL of 1% K2CO3 aqueous solution
  5. extractionextracted with CH2Cl2 (2×50 mL)
  6. washThe organic layer was then washed with water (3×50 mL)
  7. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-7fb1f64b2c844ad48b8156e53c357ed1
Source dataset
uspto-grants-1998_04
Patent number
US05736523

Reaction notes

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