HCID 54134676, compound → HCID 19906380, compound

HRID 2371815Notes

Reaction equation

HRID 2371815 reaction equation
[CH3:1][N:2]([CH3:32])[C:3]([CH2:5][CH2:6][CH:7]=[CH:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][CH:15]=[C:16]2[CH2:19][C:20]2[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][C:21]=2[O:30][CH3:31])=[CH:11][CH:10]=1)=[O:4]>[Pd].C(OCC)(=O)C>[CH3:32][N:2]([CH3:1])[C:3]([CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][CH:15]=[C:16]2[CH2:19][C:20]2[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][C:21]=2[O:30][CH3:31])=[CH:11][CH:10]=1)=[O:4]

Participants

4

Reactant 1

HCID 54134676HCID 54134676, compound

Product 1

HCID 19906380HCID 19906380, compoundYield 104.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl 4-[7-[4-(dimethylcarbamoyl)but-1-enyl]naphth-1-ylmethyl]-3-methoxybenzoate (1.1 g), 10% w/w palladium-on-carbon/50% water (110 mg) and ethyl acetate (10 ml) was hydrogenated under atmospheric pressure for 4 hours. Filtration through diatomaceous earth with ethyl acetate wash and evaporation afforded methyl 4-[7-(4-dimethylcarbamoylbutyl)naphth-1-ylmethyl]-3-methoxybenzoate (1.15 g, quantitative) as a light yellow syrup; MS(CI), m/e=434(M+H).

Workup

  1. filtrationFiltration through diatomaceous earth with ethyl acetate
  2. washwash
  3. customevaporation

Sources & evidence

ORD record
ord-adf18c114a8648d69ed197da98e97cbb
Source dataset
uspto-grants-1992_03
Patent number
US05095038

Reaction notes

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