Water → Methyl 6-(3,3,3-trifluoropropyl)nicotinate

HRID 623500Notes

Reaction equation

HRID 623500 reaction equation
[F:1][C:2]([F:8])([F:7])[CH2:3][CH2:4][Mg]Br.Cl[C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][N:11]=1.CN1CCCC1=O.O>O1CCCC1.C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.[Fe+3]>[F:1][C:2]([F:8])([F:7])[CH2:3][CH2:4][C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][N:11]=1

Participants

7

Reactant 4

HCID 962WaterHCID 13387N-methyl-2-pyrrolidoneHCID 254249Methyl 6-chloropyridine-3-carboxylateHCID 178506320HCID 178506320, compound

Product 1

HCID 67510807Methyl 6-(3,3,3-trifluoropropyl)nicotinateYield 99.9%

Reagents, catalysts & solvents 2

HCID 5483663Ferric acetylacetonateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

(3,3,3-trifluoropropyl)magnesium bromide (8.16 mL, 8.16 mmol, Step-1) is added to a solution of methyl 6-chloronicotinate (0.70 g, 4.08 mmol), iron(III) acetylacetonate (0.14 g, 0.41 mmol) and 1-methyl-2-pyrrolidinone (0.23 mL, 2.39 mmol) in tetrahydrofuran (23 mL) and stirred at room temperature for 30 minutes. The reaction mixture is poured into water, extracted with ethyl acetate and dried over sodium sulfate and concentrated in vacuo. The residue is purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (3:1) to give 0.95 g (99% yield) of the title compound as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue is purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (3:1)

Sources & evidence

ORD record
ord-c324c815f5d34eeab2c64ceb57e6b4d9
Source dataset
uspto-grants-2016_04
Patent number
US09302991B2

Reaction notes

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