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

HRID 611099
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HRID 611099 반응식
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
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참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-95c59c7bbb9e4912a85acb7273e13bea
출처 데이터셋
uspto-grants-1999_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05998433

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