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

HRID 224462
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HRID 224462 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chloride2회HCID 12794995methyl N-(2-hydroxyethyl)-3-carbomethoxypyrrole-2-acetateHCID 15930782Chloroform acetone

생성물 1

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

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a681d6bd505344ff988a3d6006ab4c1c
출처 데이터셋
uspto-grants-1980_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04232038

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