Chlorotrimethylsilane → [(1-Ethoxy-3-methylbut-1-en-1-yl)oxy](trimethyl)silane

HRID 905249Notes

Reaction equation

HRID 905249 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[C:13]([O:19][CH2:20][CH3:21])(=[O:18])[CH2:14][CH:15]([CH3:17])[CH3:16].Cl[Si:23]([CH3:26])([CH3:25])[CH3:24]>O1CCCC1>[CH3:24][Si:23]([CH3:26])([CH3:25])[O:18][C:13]([O:19][CH2:20][CH3:21])=[CH:14][CH:15]([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 7912DiisopropylamineHCID 7945Ethyl isovalerateHCID 178418339Butyllithium

Product 1

HCID 54010184[(1-Ethoxy-3-methylbut-1-en-1-yl)oxy](trimethyl)silaneYield 197.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A 2 liter flask was equipped with a mechanical stirrer, addition funnel, reflux condenser, nitrogen inlet and thermometer. The flask was dried with external heat and then charged with 563 milliliters of dry tetrahydrofuran, 75.9 grams (0.75 mol) of diisopropylamine and cooled to 0° C. Over a 30 minute period 523 milliliters of 1.6 M n-butyl lithium (0.94 mol) was added dropwise. The reaction mixture was stirred at 0° C. for 15 minutes, then cooled to -76° C. in a dry ice-acetone bath and 97.65 grams (0.75 mol) of ethyl isovalerate was added dropwise over about 30 minutes. When this addition was complete, the reaction mixture was stirred for 15 minutes at -76° C., then 205 milliliters (2.20 mol) of chlorotrimethylsilane was added dropwise. When this addition was complete, the dry ice-acetone bath was removed and the reaction mixture allowed to come to room temperature. The reaction mixture was then filtered and concentrated under reduced pressure to give a residue which was triturated with ether and filtered. The filtrate was concentrated under vacuum to give a residue and the residue was vacuum distilled through a vigreux column to give 136.44 grams (1.48 mol) of 1-trimethylsilyloxy-1-ethoxy-3-methylbutene having a boiling point of 78°-88° C. at 30 millimeters pressure.

Workup

  1. customA 2 liter flask was equipped with a mechanical stirrer, addition funnel
  2. temperaturereflux condenser, nitrogen inlet
  3. customThe flask was dried
  4. temperaturewith external heat
  5. temperaturecooled to -76° C. in a dry ice-acetone bath
  6. additionWhen this addition
  7. stirringthe reaction mixture was stirred for 15 minutes at -76° C.
  8. additionWhen this addition
  9. customthe dry ice-acetone bath was removed
  10. customto come to room temperature
  11. filtrationThe reaction mixture was then filtered
  12. concentrationconcentrated under reduced pressure
  13. customto give a residue which
  14. customwas triturated with ether
  15. filtrationfiltered
  16. concentrationThe filtrate was concentrated under vacuum
  17. customto give a residue
  18. distillationdistilled through a vigreux column

Sources & evidence

ORD record
ord-1b7c053c9e784f89bcb891bb55baa28d
Source dataset
uspto-grants-1983_12
Patent number
US04423064

Reaction notes

Loading…