Tetrahydrofuran → HCID 68527901, compound

HRID 2408462Notes

Reaction equation

HRID 2408462 reaction equation
[H-].[Na+].C1COCC1.[C:8]([O:12][C:13](=[O:21])/[CH:14]=[CH:15]/[C:16]1[CH:20]=[CH:19][NH:18][CH:17]=1)([CH3:11])([CH3:10])[CH3:9].[Br:22][C:23]1[S:27][C:26]([S:28](Cl)(=[O:30])=[O:29])=[CH:25][CH:24]=1>O>[C:8]([O:12][C:13](=[O:21])/[CH:14]=[CH:15]/[C:16]1[CH:20]=[CH:19][N:18]([S:28]([C:26]2[S:27][C:23]([Br:22])=[CH:24][CH:25]=2)(=[O:30])=[O:29])[CH:17]=1)([CH3:11])([CH3:9])[CH3:10]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydride2×HCID 27339245-Bromothiophene-2-sulfonyl chlorideHCID 66646340tert-butyl (2E)-3-(1H-pyrrol-3-yl)prop-2-enoate

Product 1

HCID 68527901HCID 68527901, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-30 °C

Procedure

A mixture of 0.53 g NaH (60%) with 40.0 ml THF is cooled down to −30° C. and 3.1 g (E)-3-(1H-pyrrol-3-yl)-acrylic acid tert-butyl ester are added. During the addition it is liberated a gas. The solution is stirred at ambient temperature for 0.5 h. Then 5.0 g of 5-bromothiophene-2-sulfonylchloride is added by −30° C. The mixture is stirred at ambient temperature for 24 h. The NaH is hydrolyzed with water and the solution is extracted with ethyl acetate. The title compound is isolated by flash chromatography. By this method 4.5 g of colorless crystals are obtained.

Workup

  1. additionDuring the addition it
  2. stirringThe mixture is stirred at ambient temperature for 24 h
  3. extractionthe solution is extracted with ethyl acetate

Sources & evidence

ORD record
ord-7a6216f9c27d4a4d86ec1d905aad8779
Source dataset
uspto-grants-2014_08
Patent number
US08815855B2

Reaction notes

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