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

HRID 611270Notes

Reaction equation

HRID 611270 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.[CH3:11][C:12]1[CH:28]=[CH:27][CH:26]=[CH:25][C:13]=1[C:14]([C:16]1[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[CH:18][CH:17]=1)=[O:15].C(N(CC)CC)C.C(P(=O)(OCC)OCC)#N>ClCCl.O>[CH3:11][C:12]1[CH:28]=[CH:27][CH:26]=[CH:25][C:13]=1[C:14]([C:16]1[CH:24]=[CH:23][C:19]([C:20]([N:8]2[CH2:9][CH2:10][C:5]3[CH:4]=[CH:3][O:2][C:6]=3[CH2:7]2)=[O:21])=[CH:18][CH:17]=1)=[O:15]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 180011004-(2-Methylbenzoyl)benzoic acidHCID 195999074,5,6,7-Tetrahydrofuro[2,3-c]pyridine hydrochloride

Product 1

HCID 196000596-[4-(2-Methylbenzoyl)benzoyl]-4,5,6,7-tetrahydrofuro[2,3-c]pyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.160 g (1.000 mmol) of 4,5,6,7-tetrahydrofuro[2,3-c]pyridine hydrochloride, 0.288 g (1.2 mmol) of 4-(2-methylbenzoyl)benzoic acid and 0.55 ml (4.0 mmol) of triethylamine in 30 ml of dichloromethane, 0.24 g (1.5 mmol) of diethyl cyanophosphonate was added dropwise under ice-cooling, followed by overnight stirring at room temperature. The reaction mixture was poured into water and extracted with dichloromethane 2 times. The combined organic layer was washed with water and 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=3/1) to yield the desired product.

Workup

  1. temperaturecooling
  2. extractionextracted with dichloromethane 2 times
  3. washThe combined organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-4619257ad63d4cb8a2972bab7162ca9c
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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