Tributylphosphine → Methyl 5-[(2-fluorobenzyl)oxy]-6-nitronicotinate

HRID 64407Notes

Reaction equation

HRID 64407 reaction equation
[OH:1][C:2]1[C:3]([N+:12]([O-:14])=[O:13])=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[F:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22]O.C(P(CCCC)CCCC)CCC.N(C(OCC)=O)=NC(OCC)=O>C1COCC1.C(OCC)(=O)C.O>[F:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][O:1][C:2]1[C:3]([N+:12]([O-:14])=[O:13])=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

8

Reactant 4

HCID 13831TributylphosphineHCID 679692-Fluorobenzylic alcoholHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 46311154HCID 46311154, compound

Product 1

HCID 86713415Methyl 5-[(2-fluorobenzyl)oxy]-6-nitronicotinate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2 g of methyl 5-hydroxy-6-nitronicotinate, 1.62 ml of (2-fluorophenyl)methanol, and 3.99 ml of tributylphosphine in 40 ml of THF was added 2.54 ml of diethyl azodicarboxylate under ice-cooling, followed by stirring for 1 hour under ice-cooling and at room temperature for 2 hours. To the reaction mixture were added water and ethyl acetate to carry out a layer separation operation. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 2.58 g of methyl 5-[(2-fluorobenzyl)oxy]-6-nitronicotinate.

Workup

  1. temperaturecooling
  2. customa layer separation operation
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8b197a627fce4032a7a2214eac100ed8
Source dataset
uspto-grants-2016_09
Patent number
US09447090B2

Reaction notes

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