Sodium Iodide → HCID 86750306, compound

HRID 1450043Notes

Reaction equation

HRID 1450043 reaction equation
[Na+].[I-].C[Si](Cl)(C)C.[C:8]([C:12]([S:14][C:15]1[C:26]2[O:25][C:24]([CH3:28])([CH3:27])[O:23][C:22]=2[C:21]([C:29]([C:54]2[C:64]3[O:65][C:66]([CH3:69])([CH3:68])[O:67][C:63]=3[C:62]([S:70][C:71]([C:73]([CH3:76])([CH3:75])[CH3:74])=[O:72])=[C:56]3[O:57][C:58]([CH3:61])([CH3:60])[O:59][C:55]=23)([C:31]2[C:41]3[O:42][C:43]([CH3:46])([CH3:45])[O:44][C:40]=3[C:39]([S:47][C:48]([C:50]([CH3:53])([CH3:52])[CH3:51])=[O:49])=[C:33]3[O:34][C:35]([CH3:38])([CH3:37])[O:36][C:32]=23)O)=[C:20]2[C:16]=1[O:17][C:18]([CH3:78])([CH3:77])[O:19]2)=[O:13])([CH3:11])([CH3:10])[CH3:9].[O-]S(S([O-])=O)=O.[Na+].[Na+]>C(#N)C>[C:73]([C:71]([S:70][C:62]1[C:63]2[O:67][C:66]([CH3:68])([CH3:69])[O:65][C:64]=2[C:54]([CH:29]([C:21]2[C:22]3[O:23][C:24]([CH3:28])([CH3:27])[O:25][C:26]=3[C:15]([S:14][C:12]([C:8]([CH3:11])([CH3:10])[CH3:9])=[O:13])=[C:16]3[O:17][C:18]([CH3:78])([CH3:77])[O:19][C:20]=23)[C:31]2[C:41]3[O:42][C:43]([CH3:45])([CH3:46])[O:44][C:40]=3[C:39]([S:47][C:48]([C:50]([CH3:53])([CH3:52])[CH3:51])=[O:49])=[C:33]3[O:34][C:35]([CH3:37])([CH3:38])[O:36][C:32]=23)=[C:55]2[C:56]=1[O:57][C:58]([CH3:61])([CH3:60])[O:59]2)=[O:72])([CH3:74])([CH3:75])[CH3:76]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 24489Sodium DithioniteHCID 86750307HCID 86750307, compound

Product 1

HCID 86750306HCID 86750306, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

NaI (0.185 g, 1.2342 mmol) and trimethylsilyl chloride (0.156 mL, 1.2336 mmol) were stirred in acetonitrile (50 mL). Tris(8-tertbutylcarbonylthio-2,2,6,6-tetramethylbenzo-[1,2-d:4,5-d']bis(1,3)dioxole-4-yl)methanol (0.220 g, 0.2056 mmol, Example 47) was added in solid form and the color of the solution became brownish. Na2S2O4 (20 mL, sat.) was added after 60 minutes and the mixture was stirred 5 minutes before separation of the phases. The aqueous phase was extracted with diethyl ether (50 mL), and the combined organic phase was dried (MgSO4) and evaporated, yielding 0.105 g (0.1168 mmol, 83%) of the title compound. Tris(8-tertbutylcarbonylthio-2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']bis(1,3)dioxole-4-yl)methane (0.205 g, 0.200 mmol, 97.3%).

Workup

  1. extractionThe aqueous phase was extracted with diethyl ether (50 mL)
  2. dry with materialthe combined organic phase was dried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-b81e9915b4234058bd39f4f1c1f9e52a
Source dataset
uspto-grants-1997_02
Patent number
US05599522

Reaction notes

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