m-Trifluoromethylphenylacetonitrile → 2-Thien-2-yl-3-oxo-4-(3-trifluoromethylphenyl)-5-amino-2,3-dihydrofuran

HRID 485616

반응식

HRID 485616 반응식
[Na].[O-]CC.[Na+].[S:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[CH:11]([OH:16])[C:12]([O:14]C)=O.[F:17][C:18]([F:29])([F:28])[C:19]1[CH:20]=[C:21]([CH2:25][C:26]#[N:27])[CH:22]=[CH:23][CH:24]=1>C(O)C.O>[S:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[CH:11]1[C:12](=[O:14])[C:25]([C:21]2[CH:22]=[CH:23][CH:24]=[C:19]([C:18]([F:28])([F:17])[F:29])[CH:20]=2)=[C:26]([NH2:27])[O:16]1

참가 물질

7

반응물 4

HCID 75360m-TrifluoromethylphenylacetonitrileHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 13682356Methyl thien-2-yl-hydroxyacetate

생성물 1

HCID 136911642-Thien-2-yl-3-oxo-4-(3-trifluoromethylphenyl)-5-amino-2,3-dihydrofuran수율 12.3%

시약·촉매·용매 2

HCID 702Ethanol용매2회HCID 962Water용매

실험 절차

A dry, 250-ml, three-neck, round-bottom flask equipped with a mechanical stirrer, addition funnel and a reflux condenser bearing a nitrogen inlet tube was charged with 4.2 g of sodium and 100 ml of absolute ethanol. To the resulting sodium ethoxide solution was added dropwise a mixture of 21.1 g of methyl thien-2-yl-hydroxyacetate and 22.7 g of m-trifluoromethylphenyl-acetonitrile in 20 ml of ethanol. The resulting mixture was heated at reflux for 4-5 hours after which time it was added to 300-400 ml of water and extracted with petroleum ether. The aqueous phase was acidified with aqueous 10 weight percent hydrochloric acid and extracted two times with diethyl ether. The ether extracts were washed twice with saturated aqueous sodium bicarbonate, dried over magnesium sulfate and concentrated in vacuo to yield a thick dark oil. This oil was triturated with 20-30% ether/petroleum ether which afforded 4.9 g of the title compound as a tan powder.

후처리

  1. customA dry, 250-ml, three-neck, round-bottom flask equipped with a mechanical stirrer, addition funnel and a reflux condenser
  2. temperatureThe resulting mixture was heated
  3. temperatureat reflux for 4-5 hours after which time it
  4. extractionextracted with petroleum ether
  5. extractionextracted two times with diethyl ether
  6. washThe ether extracts were washed twice with saturated aqueous sodium bicarbonate
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customto yield a thick dark oil
  10. customThis oil was triturated with 20-30% ether/petroleum ether which

출처 및 근거

ORD 기록
ord-fee1c62f64834886b18149b90549224d
출처 데이터셋
uspto-grants-1985_08
특허 번호
US04537623

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