Chlorotrimethylsilane → HCID 18630283, compound

HRID 1939007Notes

Reaction equation

HRID 1939007 reaction equation
[CH2:1]([NH:3][C:4](=[O:17])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:2].CN(CCN(C)C)C.[Li]C(CC)C.C1CCCCC1.[CH3:37][Si:38](Cl)([CH3:40])[CH3:39]>C1COCC1>[CH2:1]([NH:3][C:4](=[O:17])[C:5]1[C:10]([Si:38]([CH3:40])([CH3:39])[CH3:37])=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:2]

Participants

7

Reactant 5

HCID 6397ChlorotrimethylsilaneHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 8078CyclohexaneHCID 912857HCID 912857, compoundHCID 178418400CID 53628100

Product 1

HCID 18630283HCID 18630283, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

This amide (2.25 g, 10 mmol) and TMEDA (1.2 eq) in THF were mixed and cooled to -78° C. and a 1.3M s-BuLi solution in cyclohexane (2.2 eq) was added dropwise. The resulting reaction mixture was stirred at -78° C. for 30 min and TMSCl (1.2 eq) was added dropwise. The reaction was stirred at -78° C. for 30 min and allowed to warm to -30° C. The reaction was worked up in the usual manner. The crude product was purified by flash chromatography and recrystallization from hexanes to afford the title compound as a white solid (1.15 g, 39%). m.p. 159°-160° C.

Workup

  1. customThe resulting reaction mixture
  2. stirringThe reaction was stirred at -78° C. for 30 min
  3. temperatureto warm to -30° C
  4. customThe crude product was purified by flash chromatography and recrystallization from hexanes

Sources & evidence

ORD record
ord-0ceff8ba414f4786b267177f3dc93c2d
Source dataset
uspto-grants-1997_12
Patent number
US05693667

Reaction notes

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