Water → 5-benzyl-6,7-dihydro-5H-furo[3,2-c]pyridin-4-one

HRID 611426Notes

Reaction equation

HRID 611426 reaction equation
S(O[CH2:6][CH2:7][C:8]1[O:9][CH:10]=[CH:11][C:12]=1[C:13]([O:15]C)=O)(C)(=O)=O.[CH2:17]([NH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(CC)C(C)C)(C)C.O>C(#N)C>[CH2:17]([N:24]1[CH2:6][CH2:7][C:8]2[O:9][CH:10]=[CH:11][C:12]=2[C:13]1=[O:15])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7504BenzylamineHCID 81531DiisopropylethylamineHCID 19600087Methyl 2-(2-mesyloxyethyl)furan-3-carboxylate

Product 1

HCID 196002565-benzyl-6,7-dihydro-5H-furo[3,2-c]pyridin-4-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of the above crude methyl 2-(2-mesyloxyethyl)furan-3-carboxylate, 0.65 g (6.1 mmol) of benzylamine and 2.33 ml (13.4 mmol) of N,N-diisopropylethylamine in 50 ml of acetonitrile was refluxed for 1 week. The reaction mixture was poured into water and extracted with ethyl acetate 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1) to yield the desired product.

Workup

  1. extractionextracted with ethyl acetate 3 times
  2. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-6d729ca3630a4557b26bcb456965c929
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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