Chlorotrimethylsilane → HCID 13227592, compound

HRID 324005Notes

Reaction equation

HRID 324005 reaction equation
C([Li])CCC.C(NC(C)C)(C)C.[CH:13]1([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:15][CH2:14]1.Cl[Si:23]([CH3:26])([CH3:25])[CH3:24]>O1CCCC1>[CH:13]1(/[CH:16]=[C:17](\[O:19][CH2:20][CH3:21])/[O:18][Si:23]([CH3:26])([CH3:25])[CH3:24])[CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 7912DiisopropylamineHCID 12453023Ethyl cyclopropaneacetateHCID 178418339Butyllithium

Product 1

HCID 13227592HCID 13227592, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-75 °C

Procedure

A solution of n-butyllithium in hexanes (1.6M, 26 ml) was added with stirring to a solution of diisopropylamine (6.2 ml) in tetrahydrofuran (8 ml) at below −25° C. under nitrogen. After 30 min, the mixture was cooled to −75° C. and ethyl cyclopropylacetate (4.5 g) added dropwise keeping the temperature below −65° C. The mixture was then maintained below −75° C. for 3 h before chlorotrimethylsilane (3.8 ml) was added below −65° C. The reaction was allowed to warm to ambient temperature and then evaporated to dryness. The residue was slurried with hexane and filtered. The filtrate was evaporated to an orange oil which was distilled in vacuo to give the title compound (4.0 g) as a clear mobile liquid, b.p 80-82° C., 3×10−2 bar.

Workup

  1. customthe temperature below −65° C
  2. additionwas added below −65° C
  3. temperatureto warm to ambient temperature
  4. customevaporated to dryness
  5. filtrationfiltered
  6. customThe filtrate was evaporated to an orange oil which
  7. distillationwas distilled in vacuo

Sources & evidence

ORD record
ord-7e4ac2840dfa464191ce82b86dbf27bb
Source dataset
uspto-grants-2001_04
Patent number
US06215002B1

Reaction notes

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