Triethylamine → HCID 178434739, Verbindung

HRID 479298Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 479298
[CH3:1][C:2]1[C:10]([CH:11]2[O:15][N:14]=[C:13]([CH3:16])[CH2:12]2)=[C:9]([S:17]([CH3:20])(=[O:19])=[O:18])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[OH:21][C:22]1[CH2:27][CH2:26][CH2:25][C:24](=[O:28])[CH:23]=1.C(N(CC)CC)C.C[Si](C#N)(C)C>C(#N)C.O>[CH3:1][C:2]1[C:10]([CH:11]2[O:15][N:14]=[C:13]([CH3:16])[CH2:12]2)=[C:9]([S:17]([CH3:20])(=[O:19])=[O:18])[CH:8]=[CH:7][C:3]=1[C:4]([C:23]1[C:22](=[O:21])[CH2:27][CH2:26][CH2:25][C:24]=1[OH:28])=[O:5]

Komponenten

7

Edukt 4

HCID 8471Triethylamine2×HCID 82115Trimethylsilyl cyanideHCID 5357793-Hydroxycyclohex-2-enoneHCID 113130902-Methyl-3-(3-methyl-4,5-dihydroisoxazol-5-yl)-4-methylsulfonylbenzoyl chloride

Produkt 1

HCID 178434739HCID 178434739, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

A solution of 2.3 g (7.7 mmol) of 2-methyl-3-(3-methyl-4,5-dihydroisoxazol-5-yl)-4-methylsulfonylbenzoyl chloride in 50 ml of acetonitrile was added dropwise at 0-5° C. to a solution of 0.86 g (7.7 mmol) of 1-hydroxycyclohex-1-en-3-one and 2.13 ml (15.4 mmol) of triethylamine in 50 ml of acetonitrile. After the mixture had been stirred for three hours at room temperature, a further 0.64 ml (4.6 mmol) of triethylamine and 0.16 g (15 mmol) of trimethylsilyl cyanide were added and the mixture was stirred for twelve hours at room temperature. The reaction mixture was then stirred into 800 ml of water and washed with methylene chloride. The aqueous phase was then brought to pH 4 using 10% strength hydrochloric acid and extracted with methylene chloride. After the organic phase had been dried, the solvent was removed and the residue was taken up in diethyl ether and digested. The resulting residue was filtered off with suction. This gave 1.3 g (3.3 mmol; 43% of theory) of the title compounds.

Aufarbeitung

  1. stirringthe mixture was stirred for twelve hours at room temperature
  2. washwashed with methylene chloride
  3. extractionextracted with methylene chloride
  4. customAfter the organic phase had been dried
  5. customthe solvent was removed
  6. filtrationThe resulting residue was filtered off with suction

Quellen und Nachweise

ORD-Eintrag
ord-becefe8f05d342dea2306b767023e1c1
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06645919B1

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