HCID 56974754, compound → HCID 131722004, compound

HRID 1954072Notes

Reaction equation

HRID 1954072 reaction equation
C(O[CH:4](OCC)[C:5](=[O:22])[CH:6]=[CH:7][CH2:8][CH2:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[C:12]([O:20][CH3:21])[CH:11]=1)C>C(O)C.[Pd]>[CH2:14]([O:16][C:6]([O:20][CH2:12][CH3:11])([CH2:7][CH2:8][CH2:9][C:10]1[CH:11]=[C:12]([O:20][CH3:21])[C:13]([O:18][CH3:19])=[C:14]([O:16][CH3:17])[CH:15]=1)[C:5](=[O:22])[CH3:4])[CH3:13]

Participants

4

Reactant 1

HCID 56974754HCID 56974754, compound

Product 1

HCID 131722004HCID 131722004, compoundYield 178.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2 g (5.7 mmol) of 6-(3,4,5-trimethoxyphenyl)-2-keto-3-hexenal-diethylacetal in 50 ml of ethanol was added 20 mg of 10% palladium on carbon and the mixture hydrogenated at 50 psi for 8 hours. The catalyst was filtered and the ethanol evaporated to yield 1.8 g of 6-(3,4,5-trimethoxyphenyl)-2-keto-3-hexanal-diethylacetal as an oil. 1H NMR (CDCl3) δ 6.38 (s, 2 H), 4.50 (s, 1 H), 3.80 (s, 6 H), 3.76 (s, 3 H), 3.60 (q, 2 H), 3.50 (q, 2 H), 2.50 (m, 4 H), 1.60 (m, 4 H), 1.20 (t, 6 H).

Workup

  1. filtrationThe catalyst was filtered
  2. customthe ethanol evaporated

Sources & evidence

ORD record
ord-7d1a71dd48a44c1c8196bc6eb28082b6
Source dataset
uspto-grants-2000_09
Patent number
US06121280

Reaction notes

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