HCID 86702219, compound → HCID 57406587, compound

HRID 1528044Notes

Reaction equation

HRID 1528044 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]([Cl: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[Cl:38]

Participants

4

Reactant 1

HCID 86702219HCID 86702219, compound

Product 1

HCID 57406587HCID 57406587, compoundYield 9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3-benzyloxy-2-(3-fluoro-4-chlorophenyl)-5,7-dihydroxy-6,8-di(3-methyl-2-buten-1-yl)-4H-benzopyran-4-one 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 tilted and the filtrate was concentrated. The residue was purified by silica gel column chrotomagraphy (eluent:methol/dichloromethane, 1:50) to give the desired compound (11.3 mg, yield 9.0%). 1H NMR (400 MHz, CDCl3): δ=11.82 (s, 1H), 8.02-7.94 (m, 2H), 7.53 (dd, 1H, J1=8.4 Hz, J2=7.6 Hz), 6.80 (s, 1H), 6.46 (s, 1H), 5.27-5.24 (m, 2H), 3.56 (d, 2H, J=6.8 Hz), 3.47 (d, 2H, J=7.2 Hz), 1.86 (s, 3H), 1.81 (s, 3H), 1.78 (s, 3H), 1.76 (s, 3H); LC-MS (ESI) m/z 459.6 [M+H]+.

Workup

  1. concentrationthe filtrate was concentrated
  2. customThe residue was purified by silica gel column chrotomagraphy (eluent:methol/dichloromethane, 1:50)

Sources & evidence

ORD record
ord-3e30f860d6174279909328b7f1616713
Source dataset
uspto-grants-2015_07
Patent number
US09090583B2

Reaction notes

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