Cyclohexene → HCID 54018820, compound

HRID 1587052Notes

Reaction equation

HRID 1587052 reaction equation
[CH3:1][C:2]1[C:3]2[CH:16]=[C:15]3[C:10]([O:11][CH2:12][CH:13]=[CH:14]3)=[C:9]([CH3:17])[C:4]=2[O:5][C:6](=[O:8])[CH:7]=1.C1CCCCC=1>[Pd].C(O)C>[CH3:1][C:2]1[C:3]2[CH:16]=[C:15]3[C:10]([O:11][CH2:12][CH2:13][CH2:14]3)=[C:9]([CH3:17])[C:4]=2[O:5][C:6](=[O:8])[CH:7]=1

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 13803206HCID 13803206, compound

Product 1

HCID 54018820HCID 54018820, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4,10-dimethyl-2H,8H-benzo[1,2-b;5,4-b']dipyran-2-one (100 mg, 0.44 mmoles), cyclohexene (0.5 ml, 4.94 mmoles) and palladium on activated carbon (10%, 50 mg) in ethanol (25 ml) was refluxed for 5 hr. The mixture was cooled, filtered and the solvent removed under reduced pressure. The residue was recrystallized from benzene/cyclohexene to afford colorless needles of 6,7-dihydro-4,10-dimethyl-2H,8H- benzo[1,2-b;5,4-b']dipyran-2-one (40 mg, 40%), mp 162°-163° C.; 1H NMR 1.93, mult, 2H, H7 ; 2.11, s, 3H, C10 -- Me; 2.24, d, J=1.0 Hz, 3H, C4 --Me; 2.75, t, J=6.5 Hz, 2H, H6 ; 4.20, t, J=5.2 Hz, 2H, H8 ; 5.94, d, J=1.0 Hz, 1H, H3 ; 6.99, s, 1H, H5. 13C NMR 7.88, q, C10 --Me; 18.52, q, C4 --Me; 21.85, 24.86, two t, C6 and C7 ; 66.90, t, C8 ; 111.29, d, C3 ; 112.73, 112.84, two d, C5a and C10 ; 118.31, s, C4a ; 122.078, d, C5 ; 150.92, s, C9a ; 152.55, s, C4 ; 155.74, s, C10a ; 161.54, s, C2.

Workup

  1. temperaturewas refluxed for 5 hr
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. customthe solvent removed under reduced pressure
  5. customThe residue was recrystallized from benzene/cyclohexene

Sources & evidence

ORD record
ord-b7bc3ad0ad584eaca83df926fc4a1c43
Source dataset
uspto-grants-1993_06
Patent number
US05216176

Reaction notes

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