Water → Bis-(2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dioxol-4-yl)-mono-(2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dithiole-4-yl)methanol

HRID 2597Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2597
[CH3:1][C:2]1([CH3:16])[O:6][C:5]2[CH:7]=[C:8]3[O:12][C:11]([CH3:14])([CH3:13])[O:10][C:9]3=[CH:15][C:4]=2[O:3]1.[CH2:17]([Li])[CH2:18][CH2:19][CH3:20].CO[C:24]([C:26]1[C:36]2[S:37][C:38]([CH3:41])([CH3:40])[S:39][C:35]=2[CH:34]=[C:28]2[S:29][C:30]([CH3:33])([CH3:32])[S:31][C:27]=12)=[O:25].[OH2:42]>CCOCC>[CH3:13][C:11]1([CH3:14])[O:10][C:9]2[C:15]([C:24]([C:17]3[C:5]4[O:6][C:2]([CH3:16])([CH3:1])[O:3][C:4]=4[CH:20]=[C:19]4[O:42][C:9]([CH3:15])([CH3:8])[O:10][C:18]=34)([C:26]3[C:36]4[S:37][C:38]([CH3:40])([CH3:41])[S:39][C:35]=4[CH:34]=[C:28]4[S:29][C:30]([CH3:32])([CH3:33])[S:31][C:27]=34)[OH:25])=[C:4]3[O:3][C:2]([CH3:16])([CH3:1])[O:6][C:5]3=[CH:7][C:8]=2[O:12]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 109220852,2,6,6-Tetramethylbenzo[1,2-d:4,5-d']bis([1,3]dioxole)HCID 539241844-Methoxycarbonyl-(2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dithiole)HCID 178418339Butyllithium

Produkt 1

HCID 86752296Bis-(2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dioxol-4-yl)-mono-(2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dithiole-4-yl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

2,2,6,6-Tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dioxole (5.15 g, 23.2 mmol) was dissolved in dry ether (40.0 mL) in a dried, argon filled reaction vessel. The solution was cooled to 0° C. and n-butyllithium (9.29 mL, 2.5M in hexane) was added. After stirring for 15 min at ambient temperature, the mixture was cooled to 0° C. and 4-methoxycarbonyl-(2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dithiole)(4.0 g, 11.6 mmol) was added portionwise. The reaction was stirred at ambient temperature overnight. The voluminous precipitate was dissolved by addition of water (70 mL) and ether (50 mL). The organic layer was separated and the aqueous phase was washed once more with ether. The organic phase was dried (Na2SO4) and evaporated to give a semisolid residue. The product was recrystallized from acetonitrile. Yield of pure product was 5.26 g (60%).

Aufarbeitung

  1. additionfilled
  2. customreaction vessel
  3. temperaturethe mixture was cooled to 0° C.
  4. stirringThe reaction was stirred at ambient temperature overnight
  5. customThe organic layer was separated
  6. washthe aqueous phase was washed once more with ether
  7. dry with materialThe organic phase was dried (Na2SO4)
  8. customevaporated
  9. customto give a semisolid residue
  10. customThe product was recrystallized from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-760fc340b5b24bef86b0fc2c43979b8e
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05728370

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