Chlorotrimethylsilane → HCID 18630118, compound

HRID 2394851Notes

Reaction equation

HRID 2394851 reaction equation
[Li]C(CC)C.C1CCCCC1.[CH2:12]([NH:14][C:15](=[O:23])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[F:22])[CH3:13].[CH3:24][Si:25](Cl)([CH3:27])[CH3:26]>C1COCC1.CCOCC.O>[CH2:12]([NH:14][C:15](=[O:23])[C:16]1[C:21]([Si:25]([CH3:27])([CH3:26])[CH3:24])=[CH:20][CH:19]=[CH:18][C:17]=1[F:22])[CH3:13]

Participants

8

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8078CyclohexaneHCID 3315690N-ethyl-2-fluorobenzamideHCID 178418400CID 53628100

Product 1

HCID 18630118HCID 18630118, compoundYield 16%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-60 °C

Procedure

A solution of 1.3M s-BuLi in cyclohexane (20.3 mL, 26.4 mmol) was added to an ether/liquid nitrogen cooled solution of N-ethyl-2-fluorobenzamide (2.00 g, 11.98 mmol) in THF (75 mL) and ether (75 mL), maintaining the internal reaction temperature ≤-95° C. The resulting mixture was stirred at this temperature for 30 min, then TMSCl (1.43 g, 13.2 mmol) was added and the mixture warmed to -60° C. After 2 h, the reaction was poured into water (200 mL). The organic layer was dried (MgSO4), concentrated, and purified by silica gel chromatography, eluted with 3:7 ethyl acetate/hexanes, to afford 0.45 g of the title compound as a white solid, a 16% yield. m.p. 86°-87° C.

Workup

  1. temperaturemaintaining the internal reaction temperature ≤-95° C
  2. waitAfter 2 h
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography
  6. washeluted with 3:7 ethyl acetate/hexanes

Sources & evidence

ORD record
ord-7172b8a5e1724025bc80ae7681025dec
Source dataset
uspto-grants-1998_09
Patent number
US05811411

Reaction notes

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