HCID 14742758, compound → HCID 14742760, compound

HRID 1651234Notes

Reaction equation

HRID 1651234 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:15]=[C:14](OC2N(C3C=CC=CC=3)N=NN=2)[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[O:28][CH3:29])[C:7]=1[CH2:30][CH2:31][CH2:32][CH3:33])=[O:5])[CH3:2].[H][H]>O1CCCC1.C(O)C.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[O:28][CH3:29])[C:7]=1[CH2:30][CH2:31][CH2:32][CH3:33])=[O:5])[CH3:2]

Participants

6

Reactant 2

HCID 14742758HCID 14742758, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14742760HCID 14742760, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-butyl-5-methoxy-4-[(1-phenyl-1H-tetrazole-5-yl)oxy]-2-naphthalenecarboxylic acid ethyl ester in a mixture of tetrahydrofuran (25 mL) and ethanol (75 mL) was hydrogenated over 10% palladium on carbon (1.3 g) at 50° C. and three atmospheres. After the uptake of hydrogen had stopped, the catalyst was removed by filtration and the filtrate was concentrated to dryness. The resulting material was dissolved in diethyl ether (150 mL) and the solution extracted with 1N sodium hydroxide (2×50 mL). After the base extracts were backwashed with diethyl ether, the combined organic layers were dried (MgSO4) and evaporated to yield 3.6 g of 1-butyl-5-methoxy-2-naphthalenecarboxylic acid ethyl ester as an oil. A portion was distilled on a Kugelrohr apparatus (140° C.; 0.1 mm) to furnish the analytical sample. Anal. Calcd for C18H22O3 : C, 75.50; H, 7.74 Found: C, 75.02; H, 7.97

Workup

  1. customthe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated to dryness
  3. dissolutionThe resulting material was dissolved in diethyl ether (150 mL)
  4. extractionthe solution extracted with 1N sodium hydroxide (2×50 mL)
  5. dry with materialthe combined organic layers were dried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-6276800f507f4c9ab8079c674a30ca72
Source dataset
uspto-grants-1990_05
Patent number
US04927838

Reaction notes

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