Diethyl Malonate → Diethyl 2-(3-(2-fluoro-4-biphenylyl)-2-oxobutyl)malonate

HRID 256777노트

반응식

HRID 256777 반응식
[H-].[Na+].[C:3]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].Cl[CH2:15][C:16](=[O:32])[CH:17]([C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[C:21]([F:31])[CH:20]=1)[CH3:18]>CN(C)C=O>[F:31][C:21]1[CH:20]=[C:19]([CH:17]([CH3:18])[C:16](=[O:32])[CH2:15][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:3]([O:11][CH2:12][CH3:13])=[O:10])[CH:24]=[CH:23][C:22]=1[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

참가 물질

5

반응물 3

HCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 156760091-Chloro-3-(2-fluoro-4-biphenylyl)-2-butanone

생성물 1

HCID 19785556Diethyl 2-(3-(2-fluoro-4-biphenylyl)-2-oxobutyl)malonate수율 62%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

To a suspension of sodium hydride (1.88 g as 60% in oil, 47.0 mmoles) which was washed with hexane to remove mineral oil and dried, in dimethylformamide (DMF, 23 ml) was added dropwise a solution of diethyl malonate (7.52 g, 47.0 mmoles) in DMF (5 ml) at 0° C. under the stream of nitrogen gas. After elevating the temperature to 50° C., a solution of 1-chloro-3-(2-fluoro-4-biphenylyl)butan-2-one (10.0 g, 36.1 mmoles) in DMF (40 ml) was added dropwise, and the resulting mixture was stirred at the same temperature for 2 hours. The reaction mixture was poured into ice water and extracted with diethyl ether. The organic layer was washed with 1M hydrochloric acid, dried over sodium sulfate and concentrated under reduced pressure. Purification of the residue by medium pressure silica gel column chromatography gave the desired diethyl 2-(3-(2-fluoro-4-biphenylyl)-2-oxobutyl)malonate (8.98 g, 22.4 mmoles, yield 62%) as a light yellow oil.

후처리

  1. washwas washed with hexane
  2. customto remove mineral oil
  3. dry with materialdried, in dimethylformamide (DMF, 23 ml)
  4. customto 50° C.
  5. extractionextracted with diethyl ether
  6. washThe organic layer was washed with 1M hydrochloric acid
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customPurification of the residue by medium pressure silica gel column chromatography

출처 및 근거

ORD 기록
ord-3f9b270d60de4f5090a98ca469ea611f
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05258396

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