HCID 69781802, compound → HCID 22728209, compound

HRID 2086126Notes

Reaction equation

HRID 2086126 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7]([CH:25]=1)=[C:8]([CH:22]=[CH:23][CH3:24])[CH:9]=[C:10]1[C:15]=2[O:14][CH2:13][C:12]2[CH:16]=[C:17]([O:20][CH3:21])[CH:18]=[CH:19][C:11]1=2>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7]([CH:25]=1)=[C:8]([CH2:22][CH2:23][CH3:24])[CH:9]=[C:10]1[C:15]=2[O:14][CH2:13][C:12]2[CH:16]=[C:17]([O:20][CH3:21])[CH:18]=[CH:19][C:11]1=2

Participants

4

Reactant 1

HCID 69781802HCID 69781802, compound

Product 1

HCID 22728209HCID 22728209, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2,8-dimethoxy-12-propenyl-6H-dibenzo[c,h]chromene (460 mg, 1.38 mmols) and palladium (92 mg, 10% on activated carbon) in 36 ml ethyl acetate was stirred under a hydrogen balloon at room temperature for 3 hours. The reaction mixture was filtered through Celite and concentrated to give 430 mg (94%) of the title compound as a light brown solid. The analytical sample was obtained by further purification with reverse-phase preparative HPLC: mp 88-90° C.; 1H NMR (DMSO-d6): δ 1.01 (3H, t, J=7.31 Hz), 1.68-1.80 (2H, m), 2.98 (2H, t, J=7.29 Hz), 3.81 (3H, s), 3.91 (3H, s), 5.25 (2H, s), 6.93 (1H, d, J=2.53 Hz), 6.98 (1H, dd, J=8.46 Hz, J=2.04 Hz), 7.17 (1H, dd, J=9.20 Hz, J=2.38 Hz), 7.28 (1H, d, J=2.36 Hz), 7.72 (1H, s), 7.77 (1H, d, 8.57 Hz), 8.08 (1H, d, J=9.14 Hz); MS (ESI) m/z335 (M+H)+.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-eaf22546c70e4949a641b4e11cca507a
Source dataset
uspto-grants-2004_04
Patent number
US06723747B2

Reaction notes

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