1,3-Dichloro-2-butene → 6,7-Dichloro-2-(3-chloro-2-butenyl)-2,3-dihydro-5-methoxy-2-propyl-1H-inden-1-one

HRID 569277

반응식

HRID 569277 반응식
[Cl:1][C:2]1[C:10]([Cl:11])=[C:9]2[C:5]([CH2:6][CH:7]([CH2:13][CH2:14][CH3:15])[C:8]2=[O:12])=[CH:4][C:3]=1[O:16][CH3:17].[H-].[Na+].Cl[CH2:21][CH:22]=[C:23]([Cl:25])[CH3:24]>C1(C)C=CC=CC=1.CN(C)C=O>[Cl:1][C:2]1[C:10]([Cl:11])=[C:9]2[C:5]([CH2:6][C:7]([CH2:21][CH:22]=[C:23]([Cl:25])[CH3:24])([CH2:13][CH2:14][CH3:15])[C:8]2=[O:12])=[CH:4][C:3]=1[O:16][CH3:17]

참가 물질

6

반응물 3

HCID 135561,3-Dichloro-2-buteneHCID 24758Sodium hydrideHCID 136133236,7-Dichloro-2,3-dihydro-5-methoxy-2-propyl-1H-inden-1-one

생성물 1

HCID 537921436,7-Dichloro-2-(3-chloro-2-butenyl)-2,3-dihydro-5-methoxy-2-propyl-1H-inden-1-one수율 80.2%

시약·촉매·용매 2

HCID 1140Toluene용매3회HCID 6228Dimethylformamide용매

반응 조건

온도
30 °C

실험 절차

6,7-Dichloro-2,3-dihydro-5-methoxy-2-propyl-1H-inden-1-one (13.66 g, 0.05 mole) dissolved in toluene (80 ml) was added over 15 minutes with stirring under N2 to a suspension of 56% sodium hydride (2.36 g, 0.055M) in dimethylformamide (65 ml) and toluene (15 ml) at 25°. The mixture was stirred without external heat for 11/2 hours, at 50° C. for 1/2 hour and then cooled to 30° C. A solution of 1,3-dichloro-2-butene (7.81 g, 0.0625 mole) in toluene (10 ml) was added, and the mixture was heated at 50°-55° for 2 hours, poured into ice water, and extracted with diethyl ether. The organic extracts were washed with water, dried over MgSO4, concentrated under vacuum and chromatographed on silica with elution with 1/1 hexane/methylene chloride to obtain 14.5 g of product as an oil which was a mixture of cis-trans isomers.

후처리

  1. additionwas added over 15 minutes
  2. temperaturewithout external heat for 11/2 hours
  3. temperaturethe mixture was heated at 50°-55° for 2 hours
  4. extractionextracted with diethyl ether
  5. washThe organic extracts were washed with water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under vacuum
  8. customchromatographed on silica with elution with 1/1 hexane/methylene chloride

출처 및 근거

ORD 기록
ord-e50b0728f67249f8b90520b3df9d302d
출처 데이터셋
uspto-grants-1988_03
특허 번호
US04731472

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