HCID 68886853, compound → 3-Hydroxy-8-nonyl-2-(2,4,5-trimethoxyphenyl)-4H-1-benzopyran-4-one

HRID 1819563Notes

Reaction equation

HRID 1819563 reaction equation
[OH:1][C:2]1[C:11](=[O:12])[C:10]2[C:5](=[C:6]([CH2:13][CH:14]=[CH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:7]=[CH:8][CH:9]=2)[O:4][C:3]=1[C:22]1[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH3:31])=[CH:24][C:23]=1[O:32][CH3:33]>[Pd].C(OCC)(=O)C>[OH:1][C:2]1[C:11](=[O:12])[C:10]2[C:5](=[C:6]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:7]=[CH:8][CH:9]=2)[O:4][C:3]=1[C:22]1[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH3:31])=[CH:24][C:23]=1[O:32][CH3:33]

Participants

4

Reactant 1

HCID 68886853HCID 68886853, compound

Product 1

HCID 578873653-Hydroxy-8-nonyl-2-(2,4,5-trimethoxyphenyl)-4H-1-benzopyran-4-oneYield 82%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A stirring suspension of 3-hydroxy-8-non-2-enyl-2-(2,4,5-trimethoxy-phenyl)-chromen-4-one 76 (0.258 g, 0.6 mmol) and 10% palladium on carbon (0.024 g) in ethyl acetate (30 ml) was placed under an atmosphere of hydrogen for 43 hours. The reaction was filtered through celite, the residue washed with ethyl acetate and the combined filtrates concentrated in vacuo to give a grey solid. Recrystallisation (petrol:ethyl acetate 2:1) yielded 3-hydroxy-8-nonyl-2-(2,4,5-trimethoxy-phenyl)-chromen-4-one 77 (0.212 g, 82%) as an off-white solid.

Workup

  1. filtrationThe reaction was filtered through celite
  2. washthe residue washed with ethyl acetate
  3. concentrationthe combined filtrates concentrated in vacuo
  4. customto give a grey solid
  5. customRecrystallisation (petrol:ethyl acetate 2:1)

Sources & evidence

ORD record
ord-ccc0b8bf17964a8da988f84507f52ef9
Source dataset
uspto-grants-2009_10
Patent number
US07601754B2

Reaction notes

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