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

HRID 611185Notes

Reaction equation

HRID 611185 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.[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:6]2[CH2:7][N:8]([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)[CH2:9][CH2:10][C:5]=2[CH:4]=[CH:3]1

Participants

7

Reactant 4

HCID 84222-Naphthoxyacetic acidHCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 195999074,5,6,7-Tetrahydrofuro[2,3-c]pyridine hydrochloride

Product 1

HCID 196002291-(5,7-dihydro-4H-furo[2,3-c]pyridin-6-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[2,3-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 purified by recrystallization from hexane/ethyl acetate (=1/1)-dichloromethane 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. customThe resulting product was purified by recrystallization from hexane/ethyl acetate (=1/1)-dichloromethane

Sources & evidence

ORD record
ord-4335a2d03b1446bcb2bd44cb7f538442
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

Loading…