Chlorotrimethylsilane → HCID 18630167, compound

HRID 1938962Notes

Reaction equation

HRID 1938962 reaction equation
[Li]C(CC)C.C1CCCCC1.C(=O)=O.CC(C)=O.[CH2:19]([NH:21][C:22]([C:24]1[CH:28]=[CH:27][S:26][CH:25]=1)=[O:23])[CH3:20].CN(CCN(C)C)C.[CH3:37][Si:38](Cl)([CH3:40])[CH3:39]>C1COCC1>[CH2:19]([NH:21][C:22]([C:24]1[CH:28]=[CH:27][S:26][C:25]=1[Si:38]([CH3:40])([CH3:39])[CH3:37])=[O:23])[CH3:20]

Participants

8

Reactant 6

HCID 6397ChlorotrimethylsilaneHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 8078CyclohexaneHCID 154523283-Thiophenecarboxamide,N-ethyl-HCID 18522661Acetone cardiceHCID 178418400CID 53628100

Product 1

HCID 18630167HCID 18630167, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

1.3M s-BuLi in cyclohexane (37.23 mL, 48.4 mmol) was added dropwise to a dry-ice/acetone cooled solution of N-ethyl-3-thiophenecarboxamide (3.41 g, 22 mmol) and TMEDA (5.62 g, 48.4 mmol) in THF (100 mL). After stirring for 30 min at -78° C., TMSCl (5.26 g, 48.4 mmol) was added in a single portion. The reaction was allowed to slowly warm to -10° C. over 1 h, then was quenched with dilute aq citric acid and extracted with ethyl acetate (3×). The combined organic solutions were dried (MgSO4), concentrated, and purified by HPLC with 3:7 EtOAc/hexanes to give 1.4 g of the title compound as a white solid, a 28% yield. m.p. 114°-116° C.

Workup

  1. temperatureto slowly warm to -10° C. over 1 h
  2. customwas quenched with dilute aq citric acid
  3. extractionextracted with ethyl acetate (3×)
  4. dry with materialThe combined organic solutions were dried (MgSO4)
  5. concentrationconcentrated
  6. custompurified by HPLC with 3:7 EtOAc/hexanes

Sources & evidence

ORD record
ord-6891f16a501b4141b6c9848229b0d093
Source dataset
uspto-grants-1997_12
Patent number
US05693667

Reaction notes

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