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

HRID 611140

반응식

HRID 611140 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

HCID 195998875-(Anthraquinone-2-carbonyl)-4,5,6,7-tetrahydrofuro[3,2-c]pyridine

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-910522ee081f4da4ad176e08d0c18afd
출처 데이터셋
uspto-grants-1999_12
특허 번호
US05998433

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