Sodium Iodide → HCID 18943069, compound

HRID 400283Notes

Reaction equation

HRID 400283 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][S:7][C:8]1[C:19]2[O:18][C:17]([CH3:21])([CH3:20])[O:16][C:15]=2[C:14]([C:22]([C:47]2[C:57]3[O:58][C:59]([CH3:62])([CH3:61])[O:60][C:56]=3[C:55]([S:63][CH2:64][C:65]([O:67][CH2:68][CH3:69])=[O:66])=[C:49]3[O:50][C:51]([CH3:54])([CH3:53])[O:52][C:48]=23)([C:24]2[C:34]3[O:35][C:36]([CH3:39])([CH3:38])[O:37][C:33]=3[C:32]([S:40][CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])=[C:26]3[O:27][C:28]([CH3:31])([CH3:30])[O:29][C:25]=23)O)=[C:13]2[C:9]=1[O:10][C:11]([CH3:71])([CH3:70])[O:12]2)=[O:5])[CH3:2].C[Si](Cl)(C)C.[I-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C.C(OCC)C>[CH2:45]([O:44][C:42]([CH2:41][S:40][C:32]1[C:33]2[O:37][C:36]([CH3:38])([CH3:39])[O:35][C:34]=2[C:24]([CH:22]([C:14]2[C:15]3[O:16][C:17]([CH3:21])([CH3:20])[O:18][C:19]=3[C:8]([S:7][CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])=[C:9]3[O:10][C:11]([CH3:70])([CH3:71])[O:12][C:13]=23)[C:47]2[C:57]3[O:58][C:59]([CH3:61])([CH3:62])[O:60][C:56]=3[C:55]([S:63][CH2:64][C:65]([O:67][CH2:68][CH3:69])=[O:66])=[C:49]3[O:50][C:51]([CH3:53])([CH3:54])[O:52][C:48]=23)=[C:25]2[C:26]=1[O:27][C:28]([CH3:30])([CH3:31])[O:29]2)=[O:43])[CH3:46]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 24477Sodium ThiosulfateHCID 86750304HCID 86750304, compound

Product 1

HCID 18943069HCID 18943069, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

Tris(8-ethoxycarbonylmethylthio-2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dioxole-4-yl)methanol (1.06 g, 1.01 mmol (Example 27)) was added to a solution of trimethyl silylchloride (0.767 mL, 6.07 mmol) and sodium iodide (0.91 g, 6.07 mmol) in acetonitrile (50 mL) and stirred for ten minutes. Saturated sodium thiosulfate (30 mL) was added, followed by diethylether (70 mL), and the mixture was stirred for 10 minutes. The phases were separated and the organic phase was washed with water (30 mL). The organic phase was diluted with more ether (100 mL), since crystals had started to form in the funnel. The solution was kept in the freezer over night after drying (MgSO4) and filtration. The crystals formed were removed (impurity) and the solution evaporated to dryness. The product was purified by dissolving the substance at room temperature in diispropyl ether (E. Merck 118867, 30 mL), followed by bubbling with helium. The flask was stoppered and put in the refrigerator for two and a half hours. The product was collected by filtration (glass sinter no. 3), and the mother liquor was evaporated to approximately half the volume. The total yield after collecting the second crop was 640 mg (0.621 mmol, 61%).

Workup

  1. stirringthe mixture was stirred for 10 minutes
  2. customThe phases were separated
  3. washthe organic phase was washed with water (30 mL)
  4. additionThe organic phase was diluted with more ether (100 mL), since crystals
  5. customto form in the funnel
  6. waitThe solution was kept in the freezer over night
  7. customafter drying
  8. filtration(MgSO4) and filtration
  9. customThe crystals formed
  10. customwere removed (impurity)
  11. customthe solution evaporated to dryness
  12. customThe product was purified
  13. dissolutionby dissolving the substance at room temperature in diispropyl ether (E. Merck 118867, 30 mL)
  14. customby bubbling with helium
  15. waitput in the refrigerator for two and a half hours
  16. filtrationThe product was collected by filtration (glass sinter no
  17. custom3), and the mother liquor was evaporated to approximately half the volume
  18. customThe total yield
  19. customafter collecting the second crop

Sources & evidence

ORD record
ord-009df816c0f941fd9a6855b3fdf6f5f6
Source dataset
uspto-grants-1998_10
Patent number
US05827501

Reaction notes

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