Tetrahydrofuran → (E)-3-[1-(3-Bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-acrylic acid tert-butyl ester

HRID 2408463Notes

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[CH:24]=[C:25]([S:29](Cl)(=[O:31])=[O:30])[CH:26]=[CH:27][CH:28]=1>O>[C:8]([O:12][C:13](=[O:21])/[CH:14]=[CH:15]/[C:16]1[CH:20]=[CH:19][N:18]([S:29]([C:25]2[CH:26]=[CH:27][CH:28]=[C:23]([Br:22])[CH:24]=2)(=[O:31])=[O:30])[CH:17]=1)([CH3:11])([CH3:9])[CH3:10]

Participants

Conditions

Temperature: -30 °C

Procedure

A mixture of 0.77 g NaH (60%) with 65.0 ml THF is cooled to −30° C. Then 3.2 g 3.1 g (E)-3-(1H-pyrrol-3-yl)-acrylic acid tert-butyl ester are added. During the addition there is liberated a gas. The solution is stirred at ambient temperature for 0.5 h. Finally 5.0 g 3-bromobenzenesulfonylchloride are added at −30° C. The suspension is stirred at ambient temperature for 24 h. The suspension is treated with water and the solution is extracted with ethyl acetate. The organic layer is dried over sodium sulfate and evaporated. The residue (oil) is crystallized from methanol. The crystals are dried in vacuo. By this method 5.7 g of colorless crystals are obtained.

Workup

additionDuring the addition there
stirringThe suspension is stirred at ambient temperature for 24 h
extractionthe solution is extracted with ethyl acetate
dry with materialThe organic layer is dried over sodium sulfate
customevaporated
customThe residue (oil) is crystallized from methanol
customThe crystals are dried in vacuo

Sources & evidence

ORD record: ord-aadc3963812744f696b6e4f8f373f88e
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815855B2

Reaction notes

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