Chlorotrimethylsilane → HCID 54497858, compound

HRID 2058288Notes

Reaction equation

HRID 2058288 reaction equation
C[Li].C(NC(C)C)(C)C.[CH2:10]([C:14]1[CH:19]=[CH:18][C:17]([CH:20]([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:16][CH:15]=1)[CH:11]([CH3:13])[CH3:12].Cl[Si:28]([CH3:31])([CH3:30])[CH3:29]>C(OCC)C>[CH2:24]([O:23][C:21]([O:22][Si:28]([CH3:31])([CH3:30])[CH3:29])=[C:20]([CH3:26])[C:17]1[CH:16]=[CH:15][C:14]([CH2:10][CH:11]([CH3:13])[CH3:12])=[CH:19][CH:18]=1)[CH3:25]

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 7912DiisopropylamineHCID 170486Ethyl 2-[4-(2-methylpropyl)phenyl]propanoateHCID 178418348HCID 178418348, compound

Product 1

HCID 54497858HCID 54497858, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-70 °C

Procedure

Methyllithium in diethyl ether (0.25 mol, 140 ml of 1.8 M solution) was added dropwise to a solution of 27.6 g (0.27 mol) of diisopropylamine in 40 ml of diethyl ether. The reaction mixture was cooled to -70° C. and 37.5 g (0.16 mol) of ethyl 4-isobutyl-α-methylphenylacetate were added dropwise. The reaction mixture was warmed to 0° C. and 46 ml (0.36 mol) of chlorotrimethylsilane were added. The reaction mixture was stirred overnight at 25° C., filtered and then distilled to give 34.3 g (70% yield) of β-ethoxy-4-isobutyl-α-methyl-β-(trimethylsiloxy)-styrene as a colorless liquid, bp 129°-130° C. (0.4 mm). Anal. Calcd. for C18H30O2Si: C, 70.53; H, 9.87; Found: C, 70.38; H, 9.78.

Workup

  1. temperatureThe reaction mixture was warmed to 0° C.
  2. filtrationfiltered
  3. distillationdistilled

Sources & evidence

ORD record
ord-d4626af5bf5b433dbd190cdf337bb7b9
Source dataset
uspto-grants-1980_07
Patent number
US04215044

Reaction notes

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