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Triethylamine → methyl N-(2-mesyloxyethyl)-3-carbomethoxypyrrole-2-acetate

HRID 224462
ノート
印刷プレビュー

反応式

HRID 224462 の反応式
[OH:1][CH2:2][CH2:3][N:4]1[CH:8]=[CH:7][C:6]([C:9]([O:11][CH3:12])=[O:10])=[C:5]1[CH2:13][C:14]([O:16][CH3:17])=[O:15].C(N(CC)CC)C.[CH3:25][S:26](Cl)(=[O:28])=[O:27].C(Cl)(Cl)Cl.CC(C)=O>ClCCl>[S:26]([O:1][CH2:2][CH2:3][N:4]1[CH:8]=[CH:7][C:6]([C:9]([O:11][CH3:12])=[O:10])=[C:5]1[CH2:13][C:14]([O:16][CH3:17])=[O:15])([CH3:25])(=[O:28])=[O:27]
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 8471TriethylamineHCID 31297Methanesulfonyl chloride2 回HCID 12794995methyl N-(2-hydroxyethyl)-3-carbomethoxypyrrole-2-acetateHCID 15930782Chloroform acetone

生成物 1

HCID 12795003methyl N-(2-mesyloxyethyl)-3-carbomethoxypyrrole-2-acetate収率 77.7%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

実験手順

To a stirred solution of 4.1 g of methyl N-(2-hydroxyethyl)-3-carbomethoxypyrrole-2-acetate in 35 ml of dry dichloromethane cooled to -10° C., are added 2.65 ml of triethylamine and thereafter, in a dropwise fashion, 1.46 ml of methanesulfonyl chloride, maintaining the temperature of the reaction mixture at -10° to -5° C. The course of the reaction is followed by t.l.c. analysis using chloroform:acetone (90:10). When the reaction appears to be complete (about 30 minutes after the addition of the methanesulfonyl chloride is terminated) there is added slowly 10 ml of water. The organic phase is separated, washed with water (3×30 ml), dried over sodium sulfate and evaporated under reduced pressure. Crystallization of the residue from dichloromethane affords 4.75 g (77.7%) of methyl N-(2-mesyloxyethyl)-3-carbomethoxypyrrole-2-acetate (V,R=H), m.p. 99°-101° C.

後処理

  1. customabout 30 minutes
  2. customis terminated) there
  3. additionis added slowly 10 ml of water
  4. customThe organic phase is separated
  5. washwashed with water (3×30 ml)
  6. dry with materialdried over sodium sulfate
  7. customevaporated under reduced pressure
  8. customCrystallization of the residue from dichloromethane

出典と根拠

ORDレコード
ord-a681d6bd505344ff988a3d6006ab4c1c
出典データセット
uspto-grants-1980_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04232038

反応ノート

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