Allyl bromide → alpha-(2-Propenyl)-[2-(2-nitro-6-trifluoromethylphenyl)-1-(4-methoxyphenyl)ethyl]propanedioic acid, dimethyl ester

HRID 580405노트

반응식

HRID 580405 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[C:5]=1[CH2:14][CH:15]([CH:24]([C:29]([O:31][CH3:32])=[O:30])[C:25]([O:27][CH3:28])=[O:26])[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)([O-:3])=[O:2].[H-].[Na+].[CH2:35](Br)[CH:36]=[CH2:37]>CN(C)C=O>[CH2:37]([C:24]([CH:15]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)[CH2:14][C:5]1[C:6]([C:10]([F:11])([F:12])[F:13])=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])([C:29]([O:31][CH3:32])=[O:30])[C:25]([O:27][CH3:28])=[O:26])[CH:36]=[CH2:35]

참가 물질

5

반응물 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 14156192[1-(4-Methoxyphenyl)-2-[2-nitro-6-(trifluoromethyl)phenyl]ethyl]propanedioic acid, dimethyl ester

생성물 1

HCID 15128658alpha-(2-Propenyl)-[2-(2-nitro-6-trifluoromethylphenyl)-1-(4-methoxyphenyl)ethyl]propanedioic acid, dimethyl ester수율 97.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

[2-(2-Nitro-6-trifluoromethylphenyl)-1-(4-methoxyphenyl)ethyl]propanedioic acid, dimethyl ester (14.55 g; 31.96 mmole) was dissolved in dry dimethylformamide (90 ml) under argon. Prewashed 50% sodium hydride (1.85 g; 38.5 mmole) was added with stirring and stirring was continued for 20 minutes before allyl bromide (19.33 g; 159.8 mmole; 13.8 ml; d=1.398; 5 eq.) was added dropwise. The mixture was quenched (1N hydrochloric acid) after a few minutes of reaction time, and extracted with ethyl acetate (two times). The organic extract was washed with saturated potassium carbonate (two times), saturated sodium chloride, and dried (magnesium sulfate). The solution was concentrated on a high vacuum pump leaving 23.0 g. This material was flash chromatographed (silica gel/9:1-hexane:ethyl acetate) and the appropriate fractions were combined and concentrated giving 15.45 g of the title compound as an oil.

후처리

  1. stirringstirring
  2. additionwas added dropwise
  3. customThe mixture was quenched (1N hydrochloric acid) after a few minutes
  4. customof reaction time
  5. extractionextracted with ethyl acetate (two times)
  6. extractionThe organic extract
  7. washwas washed with saturated potassium carbonate (two times), saturated sodium chloride
  8. dry with materialdried (magnesium sulfate)
  9. concentrationThe solution was concentrated on a high vacuum pump
  10. customleaving 23.0 g
  11. customchromatographed (silica gel/9:1-hexane:ethyl acetate)
  12. concentrationconcentrated

출처 및 근거

ORD 기록
ord-86832b3174454d7b859a4a3bbe2e950d
출처 데이터셋
uspto-grants-1988_06
특허 번호
US04752645

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