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Formaldehyde → 6-[4-(1-Phenylethenyl)benzoyl]-2-(1-pyrrolidinylmethyl)-4,5,6,7-tetrahydrofuro[2,3-c]pyridine

HRID 611371
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HRID 611371 반응식
[C:1]1([C:7]([C:9]2[CH:25]=[CH:24][C:12]([C:13]([N:15]3[CH2:20][CH2:19][C:18]4[CH:21]=[CH:22][O:23][C:17]=4[CH2:16]3)=[O:14])=[CH:11][CH:10]=2)=[CH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1.[CH2:31]=O>C(O)(=O)C>[C:1]1([C:7]([C:9]2[CH:25]=[CH:24][C:12]([C:13]([N:15]3[CH2:20][CH2:19][C:18]4[CH:21]=[C:22]([CH2:31][N:26]5[CH2:30][CH2:29][CH2:28][CH2:27]5)[O:23][C:17]=4[CH2:16]3)=[O:14])=[CH:11][CH:10]=2)=[CH2:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
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참가 물질

5

반응물 3

HCID 712FormaldehydeHCID 31268PyrrolidineHCID 196001706-[4-(1-Phenylethenyl)benzoyl]-4,5,6,7-tetrahydrofuro[2,3-c]pyridine

생성물 1

HCID 195999626-[4-(1-Phenylethenyl)benzoyl]-2-(1-pyrrolidinylmethyl)-4,5,6,7-tetrahydrofuro[2,3-c]pyridine

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
100 °C

실험 절차

To a solution of 0.724 g (2.198 mmol) of the above 6-[4-(1-phenylethenyl)benzoyl]-4,5,6,7-tetrahydrofuro[2,3-c]pyridine in 10 ml of acetic acid, 0.28 ml (3.30 mmol) of pyrrolidine and 0.27 g (3.30 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 1 hour. After the solvent was distilled off under reduced pressure, the residual solution was alkalified with aqueous sodium hydroxide and extracted with ethyl acetate 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 column chromatography (ethyl acetate to ethyl acetate/methanol=4/1) to yield the desired product.

후처리

  1. distillationAfter the solvent was distilled off under reduced pressure
  2. extractionextracted with ethyl acetate 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 column chromatography (ethyl acetate to ethyl acetate/methanol=4/1)

출처 및 근거

ORD 기록
ord-de2dcade8bff474fae37a56fdceaf80b
출처 데이터셋
uspto-grants-1999_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05998433

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