Methyl Nicotinate → HCID 60114309, compound

HRID 1944517Notes

Reaction equation

HRID 1944517 reaction equation
[C:1]1([O:7][C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:11][O:12][C:13](=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[N:16][CH:15]=1.[CH2:21]([Mg]Br)[CH2:22][CH2:23][CH2:24][CH3:25]>O1CCCC1>[C:1]1([O:7][C:8]([N:16]2[CH:17]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:18]=[CH:19][C:14]([C:13]([O:12][CH3:11])=[O:20])=[CH:15]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7151Methyl NicotinateHCID 15891Phenyl chloroformateHCID 178445865HCID 178445865, compound

Product 1

HCID 60114309HCID 60114309, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Phenylchloroformate (1.83 mL, 14.6 mmol) was added dropwise to a solution of Nicotinic acid methyl ester (2.0 g, 14.6 mmol) in tetrahydrofuran (30 mL) at −20° C., and stirred for ten minutes. A solution of pentylmagnesium bromide (2 M in diethyl ether, 7.3 mL, 14.6 mmol) was added dropwise to the solution and stirred for 30 min at −20° C. The resulting solution was washed successively with saturated aqueous ammonium chloride and brine. The solution was dried over sodium sulfate, and the solvent was evaporated in vacuo to give the product mixed with another isomer. The crude mixture was used without purification in the subsequent step. MS: m/z 330 (MH+).

Workup

  1. stirringstirred for 30 min at −20° C
  2. washThe resulting solution was washed successively with saturated aqueous ammonium chloride and brine
  3. dry with materialThe solution was dried over sodium sulfate
  4. customthe solvent was evaporated in vacuo
  5. customto give the product
  6. additionmixed with another isomer
  7. customThe crude mixture was used without purification in the subsequent step

Sources & evidence

ORD record
ord-a8bd79b0eb304f3d9259b3015e28538a
Source dataset
uspto-grants-2013_03
Patent number
US08394828B2

Reaction notes

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