HCID 19906366, compound → HCID 19906359, compound

HRID 2371806Notes

Reaction equation

HRID 2371806 reaction equation
[C:1]([CH2:4]/[CH:5]=[CH:6]/[C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][CH:13]=[C:14]2[CH2:17][C:18]2[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][C:19]=2[O:28][CH3:29])=[CH:9][CH:8]=1)([OH:3])=[O:2].O=C1OC(C2C=C3C(C=CC=C3CC3C=CC(C(OC)=O)=CC=3OC)=CC=2)CC1>[Pd].C(OCC)(=O)C>[C:1]([CH2:4][CH2:5][CH2:6][C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][CH:13]=[C:14]2[CH2:17][C:18]2[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][C:19]=2[O:28][CH3:29])=[CH:9][CH:8]=1)([OH:3])=[O:2]

Participants

5

Reactant 2

HCID 19906366HCID 19906366, compoundHCID 19906413HCID 19906413, compound

Product 1

HCID 19906359HCID 19906359, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl E-4-[7-(3-carboxyprop-1-enyl)naphth-1-ylmethyl]-3-methoxybenzoate and methyl 4-[7-(2,3,4,5-tetrahydro-5-oxofuran-2-yl)naphth-1-ylmethyl]-3-methoxybenzoate (2.52 g), ethyl acetate (70 ml) and 10% (w/w) palladium on carbon (0.25 g) was hydrogenated under atmospheric pressure for 18 h. The reaction mixture was filtered through diatomaceous earth with ethyl acetate wash. The filtrate was evaporated to give methyl 4-[7-(3-carboxypropyl)naphth-1-ylmethyl]-3-methoxybenzoate (2.42 g, 96%) as a yellow foam; MS(CI), m/e=392(M+H).

Workup

  1. filtrationThe reaction mixture was filtered through diatomaceous earth with ethyl acetate
  2. washwash
  3. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-64db41d4f90b42bf90fcbeb4d1ee0835
Source dataset
uspto-grants-1992_03
Patent number
US05095038

Reaction notes

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