1-Penten-3-one → 9-Carbamoyl-9-(3-oxopentyl)fluorene

HRID 542642

반응식

HRID 542642 반응식
[C:1]([CH:4]1[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2)(=[O:3])[NH2:2].[OH-].C([N+](CC)(CC)CC)C1C=CC=CC=1.[CH:32]([C:34]([CH2:36][CH3:37])=[O:35])=[CH2:33]>O1CCCC1>[C:1]([C:4]1([CH2:33][CH2:32][C:34](=[O:35])[CH2:36][CH3:37])[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2)(=[O:3])[NH2:2]

참가 물질

5

반응물 3

HCID 153941-Penten-3-oneHCID 74601Benzyltriethylammonium hydroxideHCID 3450289H-fluorene-9-carboxamide

생성물 1

HCID 138534899-Carbamoyl-9-(3-oxopentyl)fluorene

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
25 °C

실험 절차

A solution of 52.3 g. of 9-carbamoylfluorene and 10 ml. of benzyltriethylammonium hydroxide in 700 ml. of tetrahydrofuran was heated at 45° C. for thirty minutes and then cooled to 25° C. The reaction mixture was diluted by addition in one portion of 25.2 g. of ethyl vinyl ketone. The reaction mixture was stirred at 25° C. for sixteen hours and at reflux for three hours. The mixture was cooled, added to 200 g. of ice and extracted with 50% ethyl acetate-diethyl ether. The organic extract was washed with water, with 10% sodium hydroxide, dried and the solvent was removed by evaporation under reduced pressure. The solid residue was crystallized from ethyl acetate and petroleum ether to afford 42.6 g of 9-carbamoyl-9-(3-oxopentyl)fluorene. m.p. 133°-135° C.

후처리

  1. additionThe reaction mixture was diluted by addition in one portion of 25.2 g
  2. temperatureat reflux for three hours
  3. temperatureThe mixture was cooled
  4. additionadded to 200 g
  5. extractionof ice and extracted with 50% ethyl acetate-diethyl ether
  6. extractionThe organic extract
  7. washwas washed with water, with 10% sodium hydroxide
  8. customdried
  9. customthe solvent was removed by evaporation under reduced pressure
  10. customThe solid residue was crystallized from ethyl acetate and petroleum ether

출처 및 근거

ORD 기록
ord-e393a37013b4496cacbd45c5bcb44433
출처 데이터셋
uspto-grants-1987_04
특허 번호
US04658061

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