Chlorotrimethylsilane → Trimethyl-(2-methyl-1-methylene-propoxy)-silane

HRID 1009050Notes

Reaction equation

HRID 1009050 reaction equation
[Li+].CC([N-]C(C)C)C.C1COCC1.CCCCCC.Cl[Si:21]([CH3:24])([CH3:23])[CH3:22].[CH3:25][CH:26]([CH3:30])[C:27](=[O:29])[CH3:28]>CCCCC>[CH3:22][Si:21]([CH3:24])([CH3:23])[O:29][C:27](=[CH2:28])[CH:26]([CH3:30])[CH3:25]

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 112513-Methyl-2-butanoneHCID 2724682Lithium diisopropylamideHCID 21883165Tetrahydrofuran hexane

Product 1

HCID 10964789Trimethyl-(2-methyl-1-methylene-propoxy)-silane

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

To freshly prepared LDA-solution in THF/hexane (1.05 eq.) was added slowly at −78° C. chloro-trimethyl-silane 7.59 mL, 60 mmol, 1.2 eq.), followed by 3-methyl-butan-2-one 5.32 mL, 50 mmol). The reaction vessel was kept for 30 Min. at −78° C. and then allowed to reach RT. The reaction mixture was diluted with 200 mL of pentane and filtered. All volatile solvents were then evaporated from the filtrate and the residue distilled in vacuo (50 mbar, bp. 40-45° C.) to give 4.38 g of regioisomerically pure title compound as colorless liquid.

Workup

  1. customat −78° C.
  2. customto reach RT
  3. filtrationfiltered
  4. customAll volatile solvents were then evaporated from the filtrate
  5. distillationthe residue distilled in vacuo (50 mbar, bp. 40-45° C.)

Sources & evidence

ORD record
ord-6c4b355e67604ce687f0938fd96c51a5
Source dataset
uspto-grants-2011_07
Patent number
US07973051B2

Reaction notes

Loading…