2-Methoxyethanol → HCID 15180743, compound

HRID 345952Notes

Reaction equation

HRID 345952 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:9]=[CH:8][N:7](S(C2C=CC(C)=CC=2)(=O)=O)[CH:6]=1)=[O:4].[CH3:20][O:21][CH2:22][CH2:23][OH:24].[Br-].[Li+].[OH-].[Na+]>[Cl-].[Na+].O>[CH3:20][O:21][CH2:22][CH2:23][O:24][CH2:2][C:3]([C:5]1[CH:9]=[CH:8][NH:7][CH:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 80192-MethoxyethanolHCID 14798Sodium HydroxideHCID 82050Lithium BromideHCID 151807422-Chloro-1-[1-(4-methylbenzene-1-sulfonyl)-1H-pyrrol-3-yl]ethan-1-one

Product 1

HCID 15180743HCID 15180743, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

In a 100 cm3 three neck flask fitted with a thermometer, a condenser with a bubbler and an argon inlet, 2.35 g of 3-chloroacetyl-l-tosyl pyrrole 3 (8 mmoles) was introduced together with 50 cm3 of 2-methoxy ethanol. 3 g of lithium bromide was added and the solution was set under reflux and argon flux during 24 hours. After cooling, 20 cm3 of 5 N aqueous solution of sodium hydroxide was added and the mixture was maintained under stirring at ambient temperature during 24 hours. 20 cm3 of brine was added and after decantation, the aqueous layer was extracted with ethyl acetate. The combine organic layer was washed with brine, dried and evaporated. The crude product (1.4 g) was dissolved in a little amount of methanol and separated on a silica gel column (150 g; 60-200 μm; eluting with 1-29-70 acetic acid-ethyl acetate-heptane) to give 0.42 g of purified product 4 (M=183, yield: 29%). NMR: (CDCl3) ppm 7.5 1H; 6.7 1H; 6.6 1H; 4.5 s 2H; 3.6 4H; 3.3 s 3H.

Workup

  1. temperatureunder reflux
  2. temperatureAfter cooling
  3. temperaturethe mixture was maintained
  4. extractionafter decantation, the aqueous layer was extracted with ethyl acetate
  5. washThe combine organic layer was washed with brine
  6. customdried
  7. customevaporated
  8. dissolutionThe crude product (1.4 g) was dissolved in a little amount of methanol
  9. customseparated on a silica gel column (150 g; 60-200 μm; eluting with 1-29-70 acetic acid-ethyl acetate-heptane)

Sources & evidence

ORD record
ord-005b4acb1b334f14b224bf0fd7087d9c
Source dataset
uspto-grants-1991_10
Patent number
US05059694

Reaction notes

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