Chlorotrimethylsilane → HCID 18630022, compound

HRID 2394853Notes

Reaction equation

HRID 2394853 reaction equation
[Li]C(CC)C.C1CCCCC1.CN(CCN(C)C)C.[F:20][C:21]1[CH:22]=[C:23]([CH:31]=[CH:32][CH:33]=1)[C:24]([N:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1)=[O:25].[CH3:34][Si:35](Cl)([CH3:37])[CH3:36]>C1COCC1.CCOCC>[F:20][C:21]1[C:22]([Si:35]([CH3:37])([CH3:36])[CH3:34])=[C:23]([C:31]([Si:35]([CH3:37])([CH3:36])[CH3:34])=[CH:32][CH:33]=1)[C:24]([N:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1)=[O:25]

Participants

8

Reactant 5

HCID 6397ChlorotrimethylsilaneHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 8078CyclohexaneHCID 4609051HCID 4609051, compoundHCID 178418400CID 53628100

Product 1

HCID 18630022HCID 18630022, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-90 °C

Procedure

A solution of 1.3M s-BuLi in cyclohexane (23.91 mL, 31.1 mmol) was added to an ether/liquid N2 cooled (-90° C.) solution of TMEDA (3.97 g, 34.2 mmol) in THF (40 mL), followed by the addition of a solution of N-(3-fluorobenzoyl)pyrrolidine (5.0 g, 25.9 mmol) in a minimum volume of THF. The resulting reaction mixture was stirred at -90° C. for 15 min, then TMSCl (6.75 g, 62.2 mmol) was added in a single portion. The reaction was warmed to RT, quenched with dilute aq citric acid, then was extracted with ether (3×). The combined ether extracts were dried (MgSO4), concentrated, and purified by HPLC with 3:7 EtOAc/hexanes to afford 0.45 g of the title compound as an oil, a 45% yield, which solidified on standing to a white solid. m.p. 97°-100° C.

Workup

  1. customThe resulting reaction mixture
  2. temperatureThe reaction was warmed to RT
  3. customquenched with dilute aq citric acid
  4. extractionwas extracted with ether (3×)
  5. dry with materialThe combined ether extracts were dried (MgSO4)
  6. concentrationconcentrated
  7. custompurified by HPLC with 3:7 EtOAc/hexanes

Sources & evidence

ORD record
ord-379f8098a9354b8f9cbfebf5275ac4f5
Source dataset
uspto-grants-1998_09
Patent number
US05811411

Reaction notes

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