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

HRID 1108176

Reaction equation

HRID 1108176 reaction equation
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

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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. Yield: 0.44 g (87%).

Workup

  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

Sources & evidence

ORD record
ord-a9ca8e9ff0ef400fb8da8ae975b3db5e
Source dataset
uspto-grants-2000_05
Patent number
US06063360

Linked notes

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