Methyl 4-[methoxy(methyl)carbamoyl]benzoate → Methyl 4-butyrylbenzoate

HRID 1160857Notes

Reaction equation

HRID 1160857 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:15]=[CH:14][C:7]([C:8](N(OC)C)=[O:9])=[CH:6][CH:5]=1.[CH2:17]([Mg]Cl)[CH2:18][CH3:19]>C1COCC1>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:5]=[CH:6][C:7]([C:8](=[O:9])[CH2:17][CH2:18][CH3:19])=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 54447022Methyl 4-[methoxy(methyl)carbamoyl]benzoateHCID 178455855HCID 178455855, compound

Product 1

HCID 23143286Methyl 4-butyrylbenzoateYield 23.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-methoxy-N-methyl-terephthalamic acid methyl ester (4.56 g, 20.4 mmol) in THF (100 mL) is added PrMgCl (2.0M, 30.6 mmol) at 0° C., the reaction is warmed to room temperature, stirred overnight, quenched by NH4Cl aqueous solution, extracted with ethyl acetate. The combined organic layers are washed with brine, dried over sodium sulfate, concentrate. Column chromatography on silica gel gives the title compound (1 g, 23.7%).

Workup

  1. customquenched by NH4Cl aqueous solution
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers are washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-5cbf439611734c379144eaa3e1f2805b
Source dataset
uspto-grants-2010_10
Patent number
US07816557B2

Reaction notes

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