HCID 54335119, compound → HCID 19744860, compound

HRID 1030750Notes

Reaction equation

HRID 1030750 reaction equation
[C:1]([O:4][C:5]1[C:24]([CH2:25][CH:26]=[C:27]([CH3:29])[CH3:28])=[C:23]([O:30][CH2:31][O:32][CH3:33])[CH:22]=[C:21]([O:34][CH2:35][O:36][CH3:37])[C:6]=1[C:7](=[O:20])[CH:8]=[CH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][O:18][CH3:19])=[CH:12][CH:11]=1)(=[O:3])[CH3:2].[H][H]>C(O)C.[Pd]>[C:1]([O:4][C:5]1[C:24]([CH2:25][CH:26]=[C:27]([CH3:28])[CH3:29])=[C:23]([O:30][CH2:31][O:32][CH3:33])[CH:22]=[C:21]([O:34][CH2:35][O:36][CH3:37])[C:6]=1[C:7](=[O:20])[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][O:18][CH3:19])=[CH:12][CH:11]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 54335119HCID 54335119, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19744860HCID 19744860, compoundYield 46.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Conditions

Temperature
0 °C

Procedure

An ethanol solution (100 ml) of the 9.89 g of the 2'-acetoxy-4,4',6'-tris(methoxymethoxy)-3'-(3-methyl-2-butenyl)chalcone obtained as the intermediate in Specific Example 18 was added into a suspension of 5.0 g of 5% palladium/carbon in 70 ml of ethanol, in which a hydrogen gas had been sufficiently absorbed in advance, and hydrogen was absorbed by stirring the mixture at 0° C. under atmospheric pressure in a hydrogen gas atmosphere for 1.5 hours with 430.55 ml of a hydrogen gas. After the reaction, the reaction mixture was filtered and the solvent was removed from the filtrate by distillation. The obtained residue was subjected to the silica gel column chromatography [280 g of [230-400 mesh silica gel; n-hexane/ethyl acetate (5/1); 0.3 kg/cm2 ]. Fractions of 100 ml were collected and the 30th to 52nd fractions to obtain 4.58 g (yield=46.1%) of 1-[2-acetoxy-4,6-bis(methoxymethoxy)-3-(3-methyl-2-butenyl)phenyl]-3-(4-methoxymethoxyphenyl)-1-propanone.

Workup

  1. customhad been sufficiently absorbed in advance, and hydrogen
  2. customwas absorbed
  3. customAfter the reaction
  4. filtrationthe reaction mixture was filtered
  5. customthe solvent was removed from the filtrate by distillation
  6. customFractions of 100 ml were collected

Sources & evidence

ORD record
ord-23dc043fa3dd44f193262931c94eec7e
Source dataset
uspto-grants-1992_04
Patent number
US05106871

Reaction notes

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