Triethylamine → 1-(5,7-dihydro-4H-furo[2,3-c]pyridin-6-yl)-3-(3-phenethylphenyl) propan-1-one

HRID 611099Notes

Reaction equation

HRID 611099 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:20]=[C:21]([CH2:25][CH2:26][C:27](O)=[O:28])[CH:22]=[CH:23][CH:24]=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.[OH-].[Na+]>ClCCl>[O:2]1[C:6]2[CH2:7][N:8]([C:27](=[O:28])[CH2:26][CH2:25][C:21]3[CH:22]=[CH:23][CH:24]=[C:19]([CH2:11][CH2:12][C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)[CH:20]=3)[CH2:9][CH2:10][C:5]=2[CH:4]=[CH:3]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 76257Diethyl cyanophosphonateHCID 195999074,5,6,7-Tetrahydrofuro[2,3-c]pyridine hydrochlorideHCID 196000903-(3-Phenethylphenyl)propionic acid

Product 1

HCID 196000361-(5,7-dihydro-4H-furo[2,3-c]pyridin-6-yl)-3-(3-phenethylphenyl) propan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.163 g (1.021 mmol) of 4,5,6,7-tetrahydrofuro[2,3-c]pyridine hydrochloride, 0.29 g (1.1 mmol) of 3-(3-phenethylphenyl)propionic acid and 0.57 ml (4.1 mmol) of triethylamine in 30 ml of dichloromethane, 0.23 ml (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 aqueous sodium hydroxide and extracted with dichloromethane 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel chromatography (hexane/ethyl acetate =6/1 to 3/1) to yield the desired product.

Workup

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

Sources & evidence

ORD record
ord-95c59c7bbb9e4912a85acb7273e13bea
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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