Chlorotrimethylsilane → HCID 68606470, compound

HRID 2189168Notes

Reaction equation

HRID 2189168 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12](=[O:14])[CH3:13])[CH:2]([CH3:4])[CH3:3].Cl[Si:16]([CH3:19])([CH3:18])[CH3:17]>C1COCC1>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]([O:14][Si:16]([CH3:19])([CH3:18])[CH3:17])=[CH2:13])[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 15741847HCID 15741847, compound

Product 1

HCID 68606470HCID 68606470, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of commercially available 1-(2-isobutoxyphenyl)ethanone (10.0 g, 56.5 mmol) in THF (30 mL) was added dropwise to a stirred solution of lithium hexamethylsilylamide (1M in hexanes, 62 mL) in THF (200 mL) over a period of 30 min at 0° C. The resulting solution was stirred for an additional 15 min, and a solution of chlorotrimethylsilane (7.1 mL) in THF (8 mL) was added. The reaction mixture was stirred for 4 hours at room temperature. The mixture was concentrated. To the residue was added dichloromethane (60 mL), the mixture was filtered. The filtrate was concentrated to give (1-(2-isobutoxyphenyl)vinyloxy)trimethylsilane, that was submitted to the next step without further purification.

Workup

  1. stirringThe reaction mixture was stirred for 4 hours at room temperature
  2. concentrationThe mixture was concentrated
  3. additionTo the residue was added dichloromethane (60 mL)
  4. filtrationthe mixture was filtered
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-6b76c6edca59420da89c3e67d56b3347
Source dataset
uspto-grants-2012_12
Patent number
US08324231B2

Reaction notes

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