HCID 89896086, compound → HCID 89882652, compound

HRID 1528043Notes

Reaction equation

HRID 1528043 reaction equation
C([O:8][C:9]1[C:14](=[O:15])[C:13]2[C:16]([OH:31])=[C:17]([CH2:26][CH:27]=[C:28]([CH3:30])[CH3:29])[C:18]([OH:25])=[C:19]([CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23])[C:12]=2[O:11][C:10]=1[C:32]1[CH:37]=[CH:36][C:35]([F:38])=[C:34]([F:39])[CH:33]=1)C1C=CC=CC=1>CO.[Pd]>[F:39][C:34]1[CH:33]=[C:32]([C:10]2[O:11][C:12]3[C:19]([CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23])=[C:18]([OH:25])[C:17]([CH2:26][CH:27]=[C:28]([CH3:30])[CH3:29])=[C:16]([OH:31])[C:13]=3[C:14](=[O:15])[C:9]=2[OH:8])[CH:37]=[CH:36][C:35]=1[F:38]

Participants

4

Reactant 1

HCID 89896086HCID 89896086, compound

Product 1

HCID 89882652HCID 89882652, compoundYield 24.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3-benyloxy-2-(3,4-difluorophenyl)-5,7-dihydroxy-6,8-di(3-methyl-2-buten-1-yl)-4H-benzopyran-4-one (30 mg) was dissolved in 10 mL methanol, and 5% Pd/C (10 mg) was added. The reaction mixture was hydrogenated at 0° C. under atmospheric pressure for 5 hr. The mixture was filtered and the filtrate was concentrated. The residue was purified by silica gel column chromatography (eluent:methol/dichloromethane, 1:50) to give the desired compound (6 mg, yield 24%). 1H NMR (400 MHz, CDCl3): δ=11.94 (s, 1H), 8.08-7.98 (m, 2H), 7.31 (dd, 1H, J1=18.4 Hz, J2=8.8 Hz), 6.76 (s, 1H), 6.45 (s, 1H), 5.28-5.22 (m, 2H), 3.56 (d, 2H, J=6.8 Hz), 3.47 (d, 2H, J=7.2 Hz), 1.86 (s, 3H), 1.85 (s, 3H), 1.77 (s, 3H), 1.76 (s, 3H); LC-MS (ESI) m/z 442.9 [M+H]+.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by silica gel column chromatography (eluent:methol/dichloromethane, 1:50)

Sources & evidence

ORD record
ord-c3807bc003fc4e4d9b0b1f725bc80057
Source dataset
uspto-grants-2015_07
Patent number
US09090583B2

Reaction notes

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