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

反応式

HRID 569277 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒3 回HCID 6228Dimethylformamide溶媒

反応条件

温度
30 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e50b0728f67249f8b90520b3df9d302d
出典データセット
uspto-grants-1988_03
特許番号
US04731472

関連ノート

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