HCID 19906402, compound → HCID 19906412, compound

HRID 2371802Notes

Reaction equation

HRID 2371802 reaction equation
[C:1](/[C:4](/[CH3:29])=[CH:5]/[C:6]1[CH:15]=[C:14]2[C:9]([CH:10]=[CH:11][CH:12]=[C:13]2[CH2:16][C:17]2[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][C:18]=2[O:27][CH3:28])=[CH:8][CH:7]=1)([OH:3])=[O:2].[H][H]>[Pd].O1CCCC1>[C:1]([CH:4]([CH3:29])[CH2:5][C:6]1[CH:15]=[C:14]2[C:9]([CH:10]=[CH:11][CH:12]=[C:13]2[CH2:16][C:17]2[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][C:18]=2[O:27][CH3:28])=[CH:8][CH:7]=1)([OH:3])=[O:2]

Participants

5

Reactant 2

HCID 19906402HCID 19906402, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19906412HCID 19906412, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 10% (w/w) palladium on carbon (0.75 g) and methyl E-4-[7-(2-carboxyprop-1-enyl)naphth-1-ylmethyl]-3-methoxybenzoate (4.38 g), in tetrahydrofuran (100 ml) was hydrogenated under 3.7 bar of hydrogen for 2 h. To the reaction mixture was added a slurry of 10% (w/w) palladium on carbon (0.75 g) and tetrahydrofuran (20 ml). After hydrogenating for 2 h more, the reaction mixture was filtered through diatomaceous earth with tetrahydrofuran washes. The solvent was evaporated and the residue was dissolved in ether. Evaporation and vacuum drying overnight afforded methyl 4-[7-(2-carboxypropyl)naphth-1-ylmethyl]-3-methoxybenzoate (4.22 g, 96%) as a colorless glassy solid; mp 110.0°-129.0° C.; MS(CI), m/e=393(M+H).

Workup

  1. filtrationmore, the reaction mixture was filtered through diatomaceous earth with tetrahydrofuran washes
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in ether
  4. customEvaporation and vacuum
  5. customdrying overnight

Sources & evidence

ORD record
ord-c2b8b7075f3b41ee8d413d78b3f5c98a
Source dataset
uspto-grants-1992_03
Patent number
US05095038

Reaction notes

Loading…