Carbon Dioxide → Bis-(8-carboxy-2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)-dioxol-4-yl)-mono-(8-carboxy-2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dithiol-4-yl)methanol

HRID 1108172

Reaktionsgleichung

Reaktionsgleichung von HRID 1108172
CN(CCN(C)C)C.C([Li])(C)(C)C.[CH3:14][C:15]1([CH3:63])[O:19][C:18]2[C:20]([C:29]([C:47]3[C:57]4[O:58][C:59]([CH3:62])([CH3:61])[O:60][C:56]=4[CH:55]=[C:49]4[O:50][C:51]([CH3:54])([CH3:53])[O:52][C:48]=34)([C:31]3[C:41]4[S:42][C:43]([CH3:46])([CH3:45])[S:44][C:40]=4[CH:39]=[C:33]4[S:34][C:35]([CH3:38])([CH3:37])[S:36][C:32]=34)[OH:30])=[C:21]3[O:25][C:24]([CH3:27])([CH3:26])[O:23][C:22]3=[CH:28][C:17]=2[O:16]1.[C:64](=[O:66])=[O:65]>C1CCCCC1.CCOCC>[C:64]([C:28]1[C:22]2[O:23][C:24]([CH3:26])([CH3:27])[O:25][C:21]=2[C:20]([C:29]([C:47]2[C:48]3[O:52][C:51]([CH3:54])([CH3:53])[O:50][C:49]=3[C:55]([C:24]([OH:25])=[O:23])=[C:56]3[O:60][C:59]([CH3:62])([CH3:61])[O:58][C:57]=23)([C:31]2[C:32]3[S:36][C:35]([CH3:37])([CH3:38])[S:34][C:33]=3[C:39]([C:15]([OH:19])=[O:16])=[C:40]3[S:44][C:43]([CH3:45])([CH3:46])[S:42][C:41]=23)[OH:30])=[C:18]2[C:17]=1[O:16][C:15]([CH3:63])([CH3:14])[O:19]2)([OH:66])=[O:65]

Komponenten

7

Edukt 4

HCID 280Carbon DioxideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 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)methanolHCID 178418306HCID 178418306, Verbindung

Produkt 1

HCID 86752297Bis-(8-carboxy-2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)-dioxol-4-yl)-mono-(8-carboxy-2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dithiol-4-yl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8078CyclohexaneLösungsmittel

Versuchsvorschrift

Dry TMEDA (1.21 mL, 8.04 mmol) and t-butyllithium (5.36 mL, 1.5M in pentane) were dissolved in dry cyclohexane (12 mL) at 0° C. 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)dithiol-4-yl)methanol (0.608 g, 0.804 mmol) was then added at ambient temperature as a solid. After 20 min, solid carbon dioxide was added followed by dry ether (50 mL). After stirring for 17 h, the reaction mixture was filtered and the precipitate was dried. The acid was purified by preparative HPLC. Yield 0.285 g (40%).

Aufarbeitung

  1. filtrationthe reaction mixture was filtered
  2. customthe precipitate was dried
  3. customThe acid was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-56a0c6a20bb74d3dbca1250523b58c39
Quelldatensatz
uspto-grants-2000_05
Patentnummer
US06063360

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