Hexane → HCID 58902326, compound

HRID 1640168Notes

Reaction equation

HRID 1640168 reaction equation
[C:1]([O:5][C:6]([C:8]1[CH:13]=[C:12]([O:14][C:15]2[CH:24]=[C:23]3[C:18]([CH:19]=[CH:20][C:21]([C:25]([OH:27])=[O:26])=[CH:22]3)=[CH:17][CH:16]=2)[CH:11]=[CH:10][N:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:28][Si](C=[N+]=[N-])(C)C.CCCCCC>CO.C1(C)C=CC=CC=1>[CH3:28][O:26][C:25]([C:21]1[CH:22]=[C:23]2[C:18]([CH:17]=[CH:16][C:15]([O:14][C:12]3[CH:11]=[CH:10][N:9]=[C:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH:13]=3)=[CH:24]2)=[CH:19][CH:20]=1)=[O:27]

Participants

6

Reactant 3

HCID 8058Hexane2×HCID 167693Trimethylsilyldiazomethane2×HCID 58902286HCID 58902286, compound

Product 1

HCID 58902326HCID 58902326, compoundYield 58.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

To a solution of 7-{[2-(tert-butoxycarbonyl)pyridin-4-yl]oxy}-2-naphthoic acid (5.25 g, 14.3 mmol) in MeOH (50 mL) and toluene (50 mL), was added a solution of 2.0M trimethylsilyldiazomethane in hexane (14.3 mL, 28.7 mmol) dropwise. The reaction was allowed to stir for 5 h, after which time 2.0M trimethylsilyldiazomethane in hexane (7.17 mL, 14.3 mmol) was added. Stirring continued for an additional 1 h. The solvents were evaporated and the residue was dissolved in EtOAc and washed with saturated NaHCO3 and brine. The organic solution was dried (Na2SO4), filtered and evaporated. The residue was purified by column chromatography to give tert-butyl 4-{[7-(methoxycarbonyl)-2-naphthyl]oxy}pyridine-2-carboxylate as an off-white solid (3.18 g, 58.4%). LCMS: (FA) ES+ 380.2.

Workup

  1. stirringStirring
  2. waitcontinued for an additional 1 h
  3. customThe solvents were evaporated
  4. dissolutionthe residue was dissolved in EtOAc
  5. washwashed with saturated NaHCO3 and brine
  6. dry with materialThe organic solution was dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-67463ba0ee31451bac318deadc19f326
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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