Ethyl Acetoacetate → Ethyl 9,9-bis(4-fluorophenyl)-5-hydroxy-8-(2-ethyl-2H-tetrazol-5-yl)-3-oxo-6,8-nonadienoate

HRID 1195353노트

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HRID 1195353 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)=[C:9]([C:14]2[N:15]=[N:16][N:17]([CH2:19][CH3:20])[N:18]=2)[CH:10]=[CH:11][CH:12]=[O:13])=[CH:4][CH:3]=1.[C:28]([O:34][CH2:35][CH3:36])(=[O:33])[CH2:29][C:30]([CH3:32])=[O:31]>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)=[C:9]([C:14]2[N:15]=[N:16][N:17]([CH2:19][CH3:20])[N:18]=2)[CH:10]=[CH:11][CH:12]([OH:13])[CH2:32][C:30](=[O:31])[CH2:29][C:28]([O:34][CH2:35][CH3:36])=[O:33])=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 8868Ethyl AcetoacetateHCID 545245085,5-Bis(4-fluorophenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-2,4-pentadienal

생성물 1

HCID 86743728Ethyl 9,9-bis(4-fluorophenyl)-5-hydroxy-8-(2-ethyl-2H-tetrazol-5-yl)-3-oxo-6,8-nonadienoate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-40 °C

실험 절차

To a solution of 5,5-bis(4-fluorophenyl)-4-(2-ethyl-2H-tetrazol-5-yl)-2,4-pentadienal (2.0 g) in 20 mL of tetrahydrofuran at -40° C. was added 6.9 mL of 0.8M (5.5 mmoles) freshly prepared solution of ethyl acetoacetate dianion [described in Example 10]. The solution was stirred at -40° C. for 30 minutes and then allowed to warm to -10° C. After a total of one hour, the reaction was quenched with 1N HCl. The mixture was extracted with chloroform, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography to give 0.4 g of pure title compound. MS (EI): m/e=496 for M+.

후처리

  1. temperatureto warm to -10° C
  2. customAfter a total of one hour, the reaction was quenched with 1N HCl
  3. extractionThe mixture was extracted with chloroform
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-71704f3df0e043789eb7346b3e07cdcb
출처 데이터셋
uspto-grants-1992_05
특허 번호
US05110940

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