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Hexane → Ethyl 1-(2-acetoxyethyl)-4-chloropyrrole-2-glyoxalate

HRID 67112
ノート
印刷プレビュー

反応式

HRID 67112 の反応式
[C:1]([O:4][CH2:5][CH2:6][N:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[C:12](=[O:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14])(=[O:3])[CH3:2].S(Cl)([Cl:22])(=O)=O.CCCCCC.C(OCC)(=O)C>ClCCl>[C:1]([O:4][CH2:5][CH2:6][N:7]1[CH:11]=[C:10]([Cl:22])[CH:9]=[C:8]1[C:12](=[O:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14])(=[O:3])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 24648Sulfuryl chlorideHCID 12795013Ethyl 1-(2-acetoxyethyl)pyrrole-2-glyoxalate

生成物 1

HCID 12795026Ethyl 1-(2-acetoxyethyl)-4-chloropyrrole-2-glyoxalate収率 41%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane
溶媒

実験手順

The resulting ethyl 1-(2-acetoxyethyl)pyrrole-2-glyoxalate prepared as in Preparation I (40.5 g, 0.16 mol.) is dissolved in anhydrous dichloromethane (900 ml.) and cooled to -70°. Recently distilled sulfuryl chloride (13.7 ml., 0.17 mol.) is added in a dropwise manner. When the addition is completed, the solution is allowed to come to room temperature spontaneously. After two hours at this temperature TLC (silica gel; hexane:ethyl acetate; 80:20) shows the absence of starting material. The solvent is removed in vacuo and the oily residue is dissolved in dichloromethane (300 ml.) and washed to neutrality with water. The organic phase is dried over sodium sulfate and evaporated to dryness in vacuo. The residue, which weighed 63 g. is purified by column chromatography on silica gel (800 g.) using hexane ethyl acetate (90:10) as the eluting solvent. This procedure yields 19 g. (41% yield) of ethyl 1-(2-acetoxyethyl)4-chloropyrrole-2-glyoxalate (Formula V where Y is Cl) having the following physical constants:

後処理

  1. temperaturecooled to -70°
  2. additionWhen the addition
  3. customto come to room temperature
  4. customThe solvent is removed in vacuo
  5. dissolutionthe oily residue is dissolved in dichloromethane (300 ml.)
  6. washwashed
  7. dry with materialThe organic phase is dried over sodium sulfate
  8. customevaporated to dryness in vacuo
  9. customis purified by column chromatography on silica gel (800 g.)
  10. customThis procedure yields 19 g

出典と根拠

ORDレコード
ord-2bb672ac98054f02824d63ef06e85840
出典データセット
uspto-grants-1982_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04344943

反応ノート

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