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

HRID 224462
Notes
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Reaction equation

HRID 224462 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chloride2×HCID 12794995methyl N-(2-hydroxyethyl)-3-carbomethoxypyrrole-2-acetateHCID 15930782Chloroform acetone

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a681d6bd505344ff988a3d6006ab4c1c
Source dataset
uspto-grants-1980_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04232038

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes