2-Naphthoxyacetic acid → 1-(6,7-dihydro-4H-furo[3,2-c]pyridin-5-yl)-2-(2-naphthoxy)ethan-1-one

HRID 611188Notes

Reaction equation

HRID 611188 reaction equation
Cl.[O:2]1[C:10]2[CH2:9][CH2:8][NH:7][CH2:6][C:5]=2[CH:4]=[CH:3]1.[CH:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][C:12]=1[O:21][CH2:22][C:23](O)=[O:24].C(N(CC)CC)C.C(P(=O)(OCC)OCC)#N>ClCCl.O>[O:2]1[C:10]2[CH2:9][CH2:8][N:7]([C:23](=[O:24])[CH2:22][O:21][C:12]3[CH:13]=[CH:14][C:15]4[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=4)[CH:11]=3)[CH2:6][C:5]=2[CH:4]=[CH:3]1

Participants

7

Reactant 4

HCID 84222-Naphthoxyacetic acidHCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 195999414,5,6,7-Tetrahydrofuro[3,2-c]pyridine hydrochloride

Product 1

HCID 196000201-(6,7-dihydro-4H-furo[3,2-c]pyridin-5-yl)-2-(2-naphthoxy)ethan-1-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.160 g (1.000 mmol) of 4,5,6,7-tetrahydrofuro[3,2-c]pyridine hydrochloride, 0.24 g (1.2 mmol) of 2-naphthoxyacetic 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 1/1). The resulting product was washed with diethyl ether 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 to 1/1)
  7. washThe resulting product was washed with diethyl ether

Sources & evidence

ORD record
ord-01a470cb708f40739abbd05c5d6813f3
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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