Triethylamine → 6-(4-Phenethylbenzoyl)-4,5,6,7-tetrahydrofuro[2,3-c]pyridine

HRID 611353Notes

Reaction equation

HRID 611353 reaction equation
Cl.[O:2]1[C:6]2[CH2:7][NH:8][CH2:9][CH2:10][C:5]=2[CH:4]=[CH:3]1.[CH2:11]([C:19]1[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][CH:20]=1)[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C.C(P(=O)(OCC)OCC)#N>CN(C)C=O.O>[CH2:11]([C:19]1[CH:20]=[CH:21][C:22]([C:23]([N:8]2[CH2:9][CH2:10][C:5]3[CH:4]=[CH:3][O:2][C:6]=3[CH2:7]2)=[O:24])=[CH:26][CH:27]=1)[CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 104894314-(2-Phenylethyl)benzoic acidHCID 195999074,5,6,7-Tetrahydrofuro[2,3-c]pyridine hydrochloride

Product 1

HCID 196000446-(4-Phenethylbenzoyl)-4,5,6,7-tetrahydrofuro[2,3-c]pyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.552 g (3.458 mmol) of 4,5,6,7-tetrahydrofuro[2,3-c]pyridine hydrochloride, 0.78 g (3.46 mmol) of 4-phenethylbenzoic acid and 1.93 ml (13.8 mmol) of triethylamine in 15 ml of N,N-dimethylformamide, 0.63 ml (4.15 mmol) of diethyl cyanophosphonate was added dropwise, followed by overnight stirring at room temperature. This mixture was poured into water and extracted with diethyl ether 3 times. The combined organic layer was dried over anhydrous sodium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=6/1 to 3/1) to yield 6-(4-phenethylbenzoyl)-4,5,6,7-tetrahydrofuro[2,3-c]pyridine.

Workup

  1. extractionextracted with diethyl ether 3 times
  2. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=6/1 to 3/1)

Sources & evidence

ORD record
ord-5380f360fbb64ec98c2ce58989cd9b04
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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