Trimethylsilyl iodide → HCID 18687857, compound

HRID 1873193Notes

Reaction equation

HRID 1873193 reaction equation
I[Si](C)(C)C.C([O:8][P:9]([CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[C:31]3[C:32]4[CH:38]=[CH:37][CH:36]=[CH:35][C:33]=4[S:34][C:30]=3[CH:29]=[C:28]3[C:23]=2[CH:24]=[CH:25][CH:26]=[CH:27]3)=[CH:18][CH:17]=1)(=[O:13])[O:10]CC)C>C(Cl)Cl>[CH:38]1[C:32]2[C:31]3[C:22]([C:19]4[CH:20]=[CH:21][C:16]([O:15][CH2:14][P:9](=[O:8])([OH:10])[OH:13])=[CH:17][CH:18]=4)=[C:23]4[C:28](=[CH:29][C:30]=3[S:34][C:33]=2[CH:35]=[CH:36][CH:37]=1)[CH:27]=[CH:26][CH:25]=[CH:24]4

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 54330546HCID 54330546, compound

Product 1

HCID 18687857HCID 18687857, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Iodotrimethylsilane (0.78 mL, 5.49 mmol) was added to a 0-5° C., stirred solution of [4-(benzo[b]naphtho [2,3-d]thiophen-11-yl)-phenoxymethyl]-phosphonic acid diethyl ester (0.871 g, 1.83 mmol) in methylene chloride (24 mL) under a try N2 atmosphere over a period of 10 min. After 1 h, the solution was quenched with water (0.6 mL), 10% aqueous sodium carbonate (100 mL) was added and mixture was washed with methylene chloride. The aqueous layer was acidified with 10% aqueous HCl. The solid was filtered and recrystallized from methanol (75 mL) to provide the title compound as a white solid (0.65 g, 85%): mp 240-242° C.: MS (EI): [M+], 420; Anal. Calc. for C23H17O4PS: C, 65.17, H, 4.08, N, 0.00. Found: C, 63.95, H, 3.89, N, 0.41.

Workup

  1. customthe solution was quenched with water (0.6 mL), 10% aqueous sodium carbonate (100 mL)
  2. additionwas added
  3. washmixture was washed with methylene chloride
  4. filtrationThe solid was filtered
  5. customrecrystallized from methanol (75 mL)

Sources & evidence

ORD record
ord-1018f62a3b13464d841a1d4939f5ad24
Source dataset
uspto-grants-2000_08
Patent number
US06110962

Reaction notes

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