Sodium Chloride → (E)-3-[1-(toluene-4-sulfonyl)-1H-pyrrol-3-yl]-acrylic acid tert-butyl ester

HRID 1931048Notes

Reaction equation

HRID 1931048 reaction equation
[H-].[Na+].[C:3]([O:7][C:8](=[O:16])/[CH:9]=[CH:10]/[C:11]1[CH:15]=[CH:14][NH:13][CH:12]=1)([CH3:6])([CH3:5])[CH3:4].[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.[Cl-].[Na+]>O1CCCC1>[C:3]([O:7][C:8](=[O:16])/[CH:9]=[CH:10]/[C:11]1[CH:15]=[CH:14][N:13]([S:23]([C:20]2[CH:21]=[CH:22][C:17]([CH3:27])=[CH:18][CH:19]=2)(=[O:25])=[O:24])[CH:12]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 66646340tert-butyl (2E)-3-(1H-pyrrol-3-yl)prop-2-enoate2×

Product 1

HCID 66646193(E)-3-[1-(toluene-4-sulfonyl)-1H-pyrrol-3-yl]-acrylic acid tert-butyl esterYield 88.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.230 g of sodium hydride (60%) is suspended in 6 ml of tetrahydrofurane under nitrogen at −30° C. 1.01 g of (E)-3-(1H-pyrrol-3-yl)acrylic acid tert-butyl ester (compound D1) are added to the suspension and warmed slowly to room temperature and stirred for 30 minutes. Afterwards it is recooled to −30° C. and 1.19 g of p-toluenesulfonylchloride are added and stirred for 2.5 hours. The suspension is warmed slowly at room temperature and 40 ml of saturated aqueous sodium chloride solution are added. The mixture is extracted with ethyl acetate. The combined organic phase is dried over sodium sulfate (Na2SO4). Afterwards it is filtered and evaporated under vacuo. The crude product is purified by silica gel flash chromatography using a gradient of hexane-ethyl acetate from 9:1 to 1:1 to give 1.60 g of the title compound as a pale yellow solid.

Workup

  1. customis recooled to −30° C.
  2. stirringstirred for 2.5 hours
  3. temperatureThe suspension is warmed slowly at room temperature
  4. extractionThe mixture is extracted with ethyl acetate
  5. dry with materialThe combined organic phase is dried over sodium sulfate (Na2SO4)
  6. filtrationAfterwards it is filtered
  7. customevaporated under vacuo
  8. customThe crude product is purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-9346957ea15a4dfe9c81a6b6e7e50c2c
Source dataset
uspto-grants-2012_05
Patent number
US08188138B2

Reaction notes

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