3-Furancarboxamide,tetrahydro-N-methoxy-N-methyl-(9CI) → HCID 21702750, compound

HRID 2202882Notes

Reaction equation

HRID 2202882 reaction equation
CON(C)[C:4]([CH:6]1[CH2:10][CH2:9][O:8][CH2:7]1)=[O:5].[CH2:12]([Mg]Br)[CH3:13]>C1COCC1>[O:8]1[CH2:9][CH2:10][CH:6]([C:4](=[O:5])[CH2:12][CH3:13])[CH2:7]1

Participants

4

Reactant 2

HCID 450845223-Furancarboxamide,tetrahydro-N-methoxy-N-methyl-(9CI)HCID 178418443HCID 178418443, compound

Product 1

HCID 21702750HCID 21702750, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of N-methoxy-N-methyltetrahydrofuran-3-carboxamide (4.1 g) in THF (40 ml) was added ethylmagnesium bromide (3 M in ether, 13.0 ml) at 0° C. The reaction mixture was then slowly warmed to room temperature and stirred for 4 h. The reaction mixture was quenched with saturated 1 M HCl (10 ml), and extracted with EtOAc. The extract was washed with brine, dried over Na2SO4 and concentrated in vacuo. The mixture was purified by silica gel column chromatography (hexane/EtOAc) to give the title compound (3.0 g) as a pale yellow liquid.

Workup

  1. customThe reaction mixture was quenched with saturated 1 M HCl (10 ml)
  2. extractionextracted with EtOAc
  3. washThe extract was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe mixture was purified by silica gel column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-fe1e8657f0f845d4b215a5629b6c4c54
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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