Dimethylformamide → Silane, [[1-(4-fluorophenyl)ethenyl]oxy]trimethyl-

HRID 2058279Notes

Reaction equation

HRID 2058279 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][CH:5]=1)=[O:3].Cl[Si:12]([CH3:15])([CH3:14])[CH3:13].C(N(CC)CC)C.CN(C)C=O>CCCCC>[F:10][C:7]1[CH:8]=[CH:9][C:4]([C:2]([O:3][Si:12]([CH3:15])([CH3:14])[CH3:13])=[CH2:1])=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 98284'-Fluoroacetophenone

Product 1

HCID 10398215Silane, [[1-(4-fluorophenyl)ethenyl]oxy]trimethyl-Yield 37%

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

A mixture of 34.56 g (0.25 mol) of 4-fluoroacetophenone, 32.6 g (0.3 mol) of chlorotrimethylsilane, 60.6 g (0.6 mol) of triethylamine and 100 ml of dimethylformamide was refluxed overnight, cooled, and diluted with 200 ml of pentane. This mixture was washed successively three times with 300 ml of cold 5% aqueous sodium bicarbonate, with cold 1.5 N hydrochloric acid, and with 5% aqueous sodium bicarbonate, dried and distilled to give 19.44 g of 1-(4-fluorophenyl)vinyloxytrimethylsilane as a colorless liquid: bp 55°-57° C. (0.12 mm); 19F NMR (CFCl3) δ-114.1 ppm (m); 1H NMR (CFCl3) δ 0.25 ppm (s, 9H), 4.35 ppm (d,J=1.5 Hz, 1H), 4.77 ppm (d,J=1.5 Hz, 1H), 6.9 ppm (m, 2H) and 7.5 ppm (m, 2H). Anal. Calcd. for C11H15FOSi: C, 62.82; H, 7.19; Found: C, 62.97; H, 7.31.

Workup

  1. temperaturewas refluxed overnight
  2. temperaturecooled
  3. washThis mixture was washed successively three times with 300 ml of cold 5% aqueous sodium bicarbonate
  4. dry with materialwith cold 1.5 N hydrochloric acid, and with 5% aqueous sodium bicarbonate, dried
  5. distillationdistilled

Sources & evidence

ORD record
ord-9afd4cda8fb341299fd444dda41a836c
Source dataset
uspto-grants-1980_07
Patent number
US04215044

Reaction notes

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