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1-(3-Chlorobenzyl)imidazole → 1-(2-Allyl-5-norbornen-2-yl)-2-(3-chlorophenyl)-2-(1-imidazolyl)-ethanol

HRID 359044
ノート
印刷プレビュー

反応式

HRID 359044 の反応式
C([Li])CCC.[Cl:6][C:7]1[CH:8]=[C:9]([CH:16]=[CH:17][CH:18]=1)[CH2:10][N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1.[CH2:19]([C:22]1([CH:29]=[O:30])[CH2:27][CH:26]2[CH2:28][CH:23]1[CH:24]=[CH:25]2)[CH:20]=[CH2:21]>CCCCCC.C1COCC1>[CH2:19]([C:22]1([CH:29]([OH:30])[CH:10]([C:9]2[CH:16]=[CH:17][CH:18]=[C:7]([Cl:6])[CH:8]=2)[N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)[CH2:27][CH:26]2[CH2:28][CH:23]1[CH:24]=[CH:25]2)[CH:20]=[CH2:21]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 122293861-(3-Chlorobenzyl)imidazoleHCID 200656362-Allyl-5-norbornen-2-aldehydeHCID 178418339Butyllithium

生成物 1

HCID 142303401-(2-Allyl-5-norbornen-2-yl)-2-(3-chlorophenyl)-2-(1-imidazolyl)-ethanol収率 38%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回
HCID 8058
Hexane
溶媒

反応条件

温度
-70 °C

実験手順

13.8 ml (20 mmol) of a 1.45 molar solution of n-butyllithium in hexane were added dropwise to a solution of 3.85 g (20 mmol) of 1-(3-chlorobenzyl)-imidazole in 40 ml of absolute THF at -70° C. After stirring for 30 minutes at -70° C., a solution of 4.39 g of 74% purity (20 mmol) 2-allyl-5-norbornen-2-aldehyde in 30 ml of absolute THF was added dropwise at about -70° C. over about 12 minutes. The further procedure was subsequently carried out as described in Example 2. The residue (9.0 g) remaining from the organic component after removing the solvent by distillation was dissolved in diisopropyl ether/hexane 2:1, whereupon crystalline product precipitated. After isolation using 20 ml of acetonitrile, this was boiled briefly, filtered off under suction after cooling the mixture, and washed with acetonitrile. 2.70 g (≅38% yield) of pure 1-(2-allyl-5-norbornen-2-yl)-2-(3-chlorophenyl)-2-(1-imidazolyl)-ethanol were obtained in the form of a mixture, comprising 2 diastereomers, of melting point 134°-135° C.

後処理

  1. customafter removing the solvent
  2. distillationby distillation
  3. dissolutionwas dissolved in diisopropyl ether/hexane 2:1
  4. customwhereupon crystalline product precipitated
  5. filtrationfiltered off under suction
  6. temperatureafter cooling the mixture
  7. washwashed with acetonitrile

出典と根拠

ORDレコード
ord-94cac9818ebc47fc8870d28fe5377af7
出典データセット
uspto-grants-1991_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04999352

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート