Phenylacetaldehyde → Benzene, [1-[(trimethylsilyl)oxy]ethenyl]-

HRID 2058285Notes

Reaction equation

HRID 2058285 reaction equation
[C:1]1([CH2:7][CH:8]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:10][Si:11]([CH3:14])([CH3:13])Cl.C(N(CC)CC)C.CN(C)C=[O:25]>CCCCC>[CH3:10][Si:11]([CH3:14])([CH3:13])[O:25][C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[CH2:8]

Participants

6

Reactant 4

HCID 998PhenylacetaldehydeHCID 6228DimethylformamideHCID 6397ChlorotrimethylsilaneHCID 8471Triethylamine

Product 1

HCID 117406Benzene, [1-[(trimethylsilyl)oxy]ethenyl]-

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

A mixture of 30.0 g (0.25 mol) of phenylacetaldehyde, 32.6 g (0.3 mol) of trimethylchlorosilane, 60.6 g (0.6 mol) of triethylamine, and 100 ml of N,N-dimethylformamide was refluxed overnight, cooled and diluted with 200 ml of pentane. The mixture was washed successively with cold 5% aqueous sodium bicarbonate, 1.5 N hydrochloric acid, and 5% aqueous sodium bicarbonate, dried (over MgSO4), and then distilled to give 21.15 g of α-trimethylsiloxystyrene as a colorless liquid: bp 80°-83.5° C. (3.8 mm); 1H NMR (CDCl3) δ 0.07 ppm (s, 9H), 5.87 ppm (d,J=12 Hz, 1H), 6.80 ppm (d,J=12 Hz, 1H) and 7.03 ppm (m, 5H).

Workup

  1. temperaturewas refluxed overnight
  2. temperaturecooled
  3. washThe mixture was washed successively with cold 5% aqueous sodium bicarbonate, 1.5 N hydrochloric acid, and 5% aqueous sodium bicarbonate
  4. dry with materialdried (over MgSO4)
  5. distillationdistilled

Sources & evidence

ORD record
ord-3b86708cbb2649c38f9b185cb91a63cc
Source dataset
uspto-grants-1980_07
Patent number
US04215044

Reaction notes

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