Tributylstannane → 5-[[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-3-[2-(acetyloxy)ethyl]-4-thiazolidinone

HRID 467194

Reaktionsgleichung

Reaktionsgleichung von HRID 467194
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([CH:16]=[C:17]2[S:21][C:20](=S)[N:19]([CH2:23][CH2:24][O:25][C:26](=[O:28])[CH3:27])[C:18]2=[O:29])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])[CH3:3].C([SnH](CCCC)CCCC)CCC.CC(N=NC(C#N)(C)C)(C#N)C>C1(C)C=CC=CC=1>[CH3:4][C:2]([C:5]1[CH:6]=[C:7]([CH:16]=[C:17]2[S:21][CH2:20][N:19]([CH2:23][CH2:24][O:25][C:26](=[O:28])[CH3:27])[C:18]2=[O:29])[CH:8]=[C:9]([C:12]([CH3:13])([CH3:14])[CH3:15])[C:10]=1[OH:11])([CH3:1])[CH3:3]

Komponenten

5

Edukt 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 541262165-{[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene}-3-[2-(acetyloxy)ethyl]-2-thioxo-4-thiazolidinone

Produkt 1

HCID 538671995-[[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-3-[2-(acetyloxy)ethyl]-4-thiazolidinoneAusbeute 59,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Under a nitrogen atmosphere, 82.2 g of 5-[[3,5bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-3-[2-(acetyloxy)ethyl]-2-thioxo-4-thiazolidinone in 950 ml of toluene was heated to 65° C. Tri-n-butyl tin hydride (219.7 g) and AIBN (4.65 g) were added and the solution heated at reflux temperature for an additional 10 minutes. After cooling, the mixture was washed with 1.25 1 of 1N hydrochloric acid followed by 500 ml of a saturated sodium chloride solution. The organic layer was stripped and allowed to stand overnight, during which time a precipitate separated. The liquid portion was decanted off, and the resulting residue was purified by chromatography over silica gel, eluting with a gradient of 25-50% of ethyl acetate in hexane. The appropriate fractions were combined and concentrated in vacuo to provide 45.7 g of the desired titled compound, m.p.=152-155° C.

Aufarbeitung

  1. temperaturethe solution heated
  2. temperatureat reflux temperature for an additional 10 minutes
  3. temperatureAfter cooling
  4. washthe mixture was washed with 1.25 1 of 1N hydrochloric acid
  5. customa precipitate separated
  6. customThe liquid portion was decanted off
  7. customthe resulting residue was purified by chromatography over silica gel
  8. washeluting with a gradient of 25-50% of ethyl acetate in hexane
  9. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-def205c12bb64c03a946e970d25c03dc
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05158966

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