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Water → ethyl(2E)-3-(2,1-benzisothiazol-4-yl)acrylate

HRID 1639851
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1639851
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[N:17]1[S:18][CH:19]=[C:20]2[C:25]([CH:26]=O)=[CH:24][CH:23]=[CH:22][C:21]=12.O>O1CCCC1>[N:17]1[S:18][CH:19]=[C:20]2[C:25](/[CH:26]=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:24][CH:23]=[CH:22][C:21]=12
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 593346042,1-Benzisothiazole-4-carboxaldehyde

Produkt 1

HCID 66720661ethyl(2E)-3-(2,1-benzisothiazol-4-yl)acrylateAusbeute 380,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
3×

Versuchsvorschrift

Under nitrogen atmosphere, to a suspension of sodium hydride (60%, 1.16 g, 26.6 mmol) in tetrahydrofuran (30 mL) was added a solution of ethyl diethylphosphonoacetate (4.83 mL, 5.41 mmol) in tetrahydrofuran (10 mL) at 0° C., and the mixture was stirred for 20 min. To the reaction mixture was added a solution of 2,1-benzisothiazole-4-carbaldehyde (3.94 g, 24.1 mmol) in tetrahydrofuran (8.3 mL), and the mixture was warmed to room temperature over 4 hr. Water was added and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=20/80) to give the title compound (4.80 g, yield 85%).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=20/80)

Quellen und Nachweise

ORD-Eintrag
ord-f420c0e651b540bea9a8013e119a4210
Quelldatensatz
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08110585B2

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