Chlorotrimethylsilane → HCID 54293478, compound

HRID 1493435Notes

Reaction equation

HRID 1493435 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.CCCCCC.[CH3:19][Si:20]([CH3:29])([CH3:28])[CH:21]([CH3:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23].Cl[Si:31]([CH3:34])([CH3:33])[CH3:32]>C1COCC1>[CH2:25]([O:24][C:22]([O:23][Si:31]([CH3:34])([CH3:33])[CH3:32])=[C:21]([Si:20]([CH3:28])([CH3:29])[CH3:19])[CH3:27])[CH3:26]

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 7912DiisopropylamineHCID 268025ethyl 2-(trimethylsilyl)propanoateHCID 178418244HCID 178418244, compound

Product 1

HCID 54293478HCID 54293478, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 21.8 mL (0.156 mole) of diisopropylamine in 100 mL of THF at 0° was added 0.156 mole of butyl lithium/hexane. After 30 minutes, the solution was cooled to -78°, and 27.19 g of ethyl 2-trimethylsilylpropionate (vide supra) was added. After 30 minutes at -78°, 17.38 g (20.3 mL, 0.16 mole) of chlorotrimethylsilane was added. The mixture was allowed to warm to ambient temperature, filtered under argon, and the filtrate was evaporated. The residue was treated with hexane and filtered. The filtrate was concentrated and distilled in a spinning band column to give, in three fractions, 29.6 g of (82% E-) [(1-ethoxy-2-trimethylsilyl-1-propenyl)oxy]-trimethylsilane, b.p 36°/0.8 mm, -43°/0.7 mm. There were no compositional differences in the three fractions. A fraction with b.p. 45°/0.7 mm was analyzed.

Workup

  1. temperaturethe solution was cooled to -78°
  2. waitAfter 30 minutes at -78°
  3. filtrationfiltered under argon
  4. customthe filtrate was evaporated
  5. additionThe residue was treated with hexane
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. distillationdistilled in a spinning band column

Sources & evidence

ORD record
ord-9e6bb8b16eb34da78887aa574c12857e
Source dataset
uspto-grants-1991_06
Patent number
US05021524

Reaction notes

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