Acetyl chloride → (Thianthrene-1,9-diyl)bis(trimethylsilane)

HRID 721971Notes

Reaction equation

HRID 721971 reaction equation
[CH3:1][Si:2]([CH3:23])([CH3:22])[C:3]1[C:16]2[S:15](=O)[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][C:13]=3[Si:18]([CH3:21])([CH3:20])[CH3:19])[S:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.C(Cl)(=O)C>CC(C)=O>[CH3:1][Si:2]([CH3:23])([CH3:22])[C:3]1[C:16]2[S:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][C:13]=3[Si:18]([CH3:21])([CH3:20])[CH3:19])[S:8][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 150826654,6-Bis(trimethylsilyl)thianthrene-5-oxide

Product 1

HCID 15270536(Thianthrene-1,9-diyl)bis(trimethylsilane)Yield 93.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 4,6-bis(trimethylsilyl)thianthrene-5-oxide (1.67 g, 4.44 mmole) and acetyl chloride (3.80 mL, 53.2 mmole) in acetone (75 mL), KI (17.00 g, 102.0 mmole) was added. After stirring at room temperature for 2 hrs, solvent was removed in vacuo and the residue was extracted with ether. The extract was washed with water and 1 M Na2S2O3 solution, dried with MgSO4, and the solvent was removed in vacuo to afford yellow oil (1.50 g, 86%). The product was eventually crystallized and used without further purification. mp 90˜91° C. (lit. 95˜96° C.). 1H NMR (300 MHz, CDCl3) δ: 7.47 (dd, 2H, J=7.5, 1.5 Hz), 7.42 (dd, 2H, J=7.5, 1.2 Hz), 7.20 (dd, 2H, J=7.5, 7.5 Hz), 0.46 (s, 18H). 13C NMR (125 MHz, CDCl3) δ: 142.4, 139.8, 134.3, 134.0, 129.6, 126.8, 0.52. HR-MS (ESI): calcd. for C18H24S2Si2+Na 383.0750 [(M+Na)+]. found 383.0747.

Workup

  1. customsolvent was removed in vacuo
  2. extractionthe residue was extracted with ether
  3. washThe extract was washed with water and 1 M Na2S2O3 solution
  4. dry with materialdried with MgSO4
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-7322170448234de99ae802129f88feac
Source dataset
uspto-grants-2006_11
Patent number
US07138075B2

Reaction notes

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