Sodium Iodide → Tris-(2,2,6,6-tetramethylbenzo[1,2-d:5,4-d']-bis(1,3)oxathiol-4-yl) methanol

HRID 2602

Reaktionsgleichung

Reaktionsgleichung von HRID 2602
C[Si](C)(C)[C:3]1[C:16]2[O:15][C:14]([CH3:18])([CH3:17])[S:13][C:12]=2[C:11]([C:19]([C:41]2[C:49]3[S:50][C:51]([CH3:54])([CH3:53])[O:52][C:48]=3[C:47]([Si](C)(C)C)=[C:46]3[C:42]=2[S:43][C:44]([CH3:60])([CH3:59])[O:45]3)([C:21]2[C:29]3[S:30][C:31]([CH3:34])([CH3:33])[O:32][C:28]=3[C:27]([Si](C)(C)C)=[C:26]3[C:22]=2[S:23][C:24]([CH3:40])([CH3:39])[O:25]3)[OH:20])=[C:5]2[S:6][C:7]([CH3:10])([CH3:9])[O:8][C:4]=12.[I-].[Na+].Cl[Si](C)(C)C.C([O-])(O)=O.[Na+]>C(#N)C>[CH3:39][C:24]1([CH3:40])[S:23][C:22]2=[C:21]([C:19]([C:11]3[C:12]4[S:13][C:14]([CH3:18])([CH3:17])[O:15][C:16]=4[CH:3]=[C:4]4[C:5]=3[S:6][C:7]([CH3:10])([CH3:9])[O:8]4)([C:41]3[C:42]4[S:43][C:44]([CH3:59])([CH3:60])[O:45][C:46]=4[CH:47]=[C:48]4[C:49]=3[S:50][C:51]([CH3:53])([CH3:54])[O:52]4)[OH:20])[C:29]3[S:30][C:31]([CH3:33])([CH3:34])[O:32][C:28]=3[CH:27]=[C:26]2[O:25]1

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 516892Sodium BicarbonateHCID 86752300Tris-(8-trimethylsilyl-2,2,6,6-tetramethylbenzo[1,2-d:5,4-d']-bis(1,3)oxathiol-4-yl)methanol

Produkt 1

HCID 70260507Tris-(2,2,6,6-tetramethylbenzo[1,2-d:5,4-d']-bis(1,3)oxathiol-4-yl) methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Tris-(8-trimethylsilyl-2,2,6,6-tetramethylbenzo[1,2-d:5,4-d']-bis(1,3)oxathiol-4-yl)methanol (0.62 g, 0.62 mmol) was dissolved in acetonitrile (150 mL). Sodium iodide (0.75 g, 6.0 mmol) and chlorotrimethylsilane (0.65 g, 6.0 mmol) was added in one portion. The mixture was stirred for 20 min and then poured onto diethyl ether/aq. NaHCO3. The aqueous layer was extracted with ether and the combined organic layers were washed twice with water, dried (Na2SO4), evaporated, chromatographed (silica gel; dichloromethane) and finally triturated with ethyl acetate to yield the product as slightly brown crystals.

Aufarbeitung

  1. additionpoured onto diethyl ether/aq
  2. extractionThe aqueous layer was extracted with ether
  3. washthe combined organic layers were washed twice with water
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customchromatographed (silica gel; dichloromethane)
  7. customfinally triturated with ethyl acetate
  8. customto yield the product as slightly brown crystals

Quellen und Nachweise

ORD-Eintrag
ord-3f677304111d45a7802ed37ac3c6141c
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05728370

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