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

HRID 611140

Reaction equation

HRID 611140 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:24]2[C:23](=[O:25])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16](=[O:26])[C:15]=2[CH:14]=[CH:13][C:12]=1[C:27](O)=[O:28].C(N(CC)CC)C.C(P(=O)(OCC)OCC)#N>ClCCl.O>[CH:11]1[C:24]2[C:23](=[O:25])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16](=[O:26])[C:15]=2[CH:14]=[CH:13][C:12]=1[C:27]([N:7]1[CH2:8][CH2:9][C:10]2[O:2][CH:3]=[CH:4][C:5]=2[CH2:6]1)=[O:28]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 670302-Anthraquinonecarboxylic acidHCID 76257Diethyl cyanophosphonateHCID 195999414,5,6,7-Tetrahydrofuro[3,2-c]pyridine hydrochloride

Product 1

HCID 195998875-(Anthraquinone-2-carbonyl)-4,5,6,7-tetrahydrofuro[3,2-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[3,2-c]pyridine hydrochloride, 0.302 g (1.2 mmol) of anthraquinone-2-carboxylic 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 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 chromatography (hexane/ethyl acetate=2/1); the resulting solid was washed with ethyl acetate 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 chromatography (hexane/ethyl acetate=2/1)
  7. washthe resulting solid was washed with ethyl acetate

Sources & evidence

ORD record
ord-910522ee081f4da4ad176e08d0c18afd
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Linked notes

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