Chlorotrimethylsilane → HCID 86668734, compound

HRID 1424701Notes

Reaction equation

HRID 1424701 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[CH3:13][C:14](=[O:22])/[CH:15]=[CH:16]/[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].[CH3:23][Si:24](Cl)([CH3:26])[CH3:25]>C1COCC1.CCCCCC>[CH3:23][Si:24]([CH3:26])([CH3:25])[O:22][C:14](/[CH:15]=[CH:16]/[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH2:13]

Participants

7

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 7912DiisopropylamineHCID 5317045(E)-3-Nonen-2-oneHCID 178418339Butyllithium

Product 1

HCID 86668734HCID 86668734, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Procedure

Pursuant to Dienylester Formation Protocol I, diisopropylamine (7.0 mL, 50.0 mmol, 1.4 eq) and n-butyllithium (32.4 mL, 46.5 mmol, 1.3 eq, 1.44 M in hexane) in THF (33 mL) were reacted with a solution of (E)-non-3-en-2-one (5.9 mL, 35.6 mmol, 1.0 eq) in THF (10 mL) and trimethylsilylchloride (8.0 mL, 62.6 mmol, 1.8 eq) in THF (30 mL). For the silylenolether, no aqueous workup was undertaken. n-Hexane (100 mL) was added to the reaction mixture, the residue filtered off and the solvent evaporated. The raw product was purified by distillation to yield 5.54 g (26.1 mmol, 74%) of (E)-trimethyl(nona-1,3-dien-2-yloxy)silane as a colorless oil.

Workup

  1. filtrationthe residue filtered off
  2. customthe solvent evaporated
  3. distillationThe raw product was purified by distillation

Sources & evidence

ORD record
ord-e6e3e150ee014a8c98e53636ca73036c
Source dataset
uspto-grants-2015_01
Patent number
US08927750B2

Reaction notes

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