Water → HCID 66720690, Verbindung

HRID 1639837Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1639837
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[CH3:17][C:18]1[S:19][C:20]2[C:26]([CH:27]=O)=[CH:25][CH:24]=[CH:23][C:21]=2[N:22]=1.O>O1CCCC1>[CH3:17][C:18]1[S:19][C:20]2[C:26](/[CH:27]=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:25][CH:24]=[CH:23][C:21]=2[N:22]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 14835682HCID 14835682, Verbindung

Produkt 1

HCID 66720690HCID 66720690, VerbindungAusbeute 101,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

Under nitrogen atmosphere, to a suspension of 60% sodium hydride (1.26 g, 31.5 mmol) in tetrahydrofuran (50 mL) was added a solution of ethyl diethylphosphonoacetate (7.06 g, 31.5 mmol) in tetrahydrofuran (50 mL) at 0° C. and the mixture was stirred for 20 min. To the reaction mixture was added a solution of 2-methyl-1,3-benzothiazole-7-carbaldehyde (4.60 g, 26.0 mmol) in tetrahydrofuran (100 mL), and the mixture was warmed to room temperature over 2 hr. Water was added and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/1) to give the title compound (6.50 g, yield 98%).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-bed19094863949e28d3c3576be4295e3
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08110585B2

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