Chromone → 2-[6-[[3,4-Dihydro-4-oxo-8-propyl-2H-1-benzopyran-7-yl]oxy]hexyl]-6-[(6-methoxy-6-oxohexyl)oxy]benzenepropanoic Acid Methyl Ester

HRID 328025Notes

Reaction equation

HRID 328025 reaction equation
[CH3:1][O:2][C:3](=[O:49])[CH2:4][CH2:5][C:6]1[C:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][C:19]2[CH:29]=[CH:28][C:22]3[C:23](=[O:27])[CH:24]=[CH:25][O:26][C:21]=3[C:20]=2[CH2:30][CH2:31][CH2:32]C2C=CC=CC=2)=[CH:10][CH:9]=[CH:8][C:7]=1[O:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][C:45]([O:47][CH3:48])=[O:46].O1C2C(=CC=CC=2)C(=O)C=C1>[Pd].CO.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:49])[CH2:4][CH2:5][C:6]1[C:7]([O:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][C:45]([O:47][CH3:48])=[O:46])=[CH:8][CH:9]=[CH:10][C:11]=1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:29]=[CH:28][C:22]2[C:23](=[O:27])[CH2:24][CH2:25][O:26][C:21]=2[C:20]=1[CH2:30][CH2:31][CH3:32]

Participants

5

Reactant 2

HCID 10286ChromoneHCID 538678932-[(6-Methoxy-6-oxohexyl)oxy]-6-[6-[[4-oxo-8-(3-phenylpropyl)-4H-1-benzopyran-7-yl]oxy]hexyl]benzenepropanoic Acid Methyl Ester

Product 1

HCID 541909932-[6-[[3,4-Dihydro-4-oxo-8-propyl-2H-1-benzopyran-7-yl]oxy]hexyl]-6-[(6-methoxy-6-oxohexyl)oxy]benzenepropanoic Acid Methyl EsterYield 38%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

A 1.0 g (1.49 mmol) sample of 2-[(6-methoxy-6-oxohexyl)oxy]-6-[6-[[4-oxo-8-(3-phenylpropyl)-4H-1-benzopyran-7-yl]oxy]hexyl]benzenepropanoic acid methyl ester from the preceding example was catalytically hydrogenate over 10% palladium on carbon, in 30 mL of 1:1 methanol-ethyl acetate, at room temperature and 1 atmosphere, using thin layer chromatography to monitor the reduction of the starting chromone. The catalyst was filtered and the filtrate was concentrated in vacuo giving an oily product which was purified by flash-chromatography. There was obtained 0.38 g (38%) of the title chromanone as a colorless oil.

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customgiving an oily product which
  4. customwas purified by flash-chromatography

Sources & evidence

ORD record
ord-be1c3294c4da460286c65516666d2c21
Source dataset
uspto-grants-1993_12
Patent number
US05273999

Reaction notes

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