Chlorotrimethylsilane → HCID 11425908, compound

HRID 864731Notes

Reaction equation

HRID 864731 reaction equation
[CH2:1]([N:3]([CH2:14][CH3:15])[C:4](=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][CH3:12])[CH3:2].[Li+].CC([N-]C(C)C)C.C(=O)=O.CC(C)=O.[CH3:31][Si:32](Cl)([CH3:34])[CH3:33]>C1COCC1>[CH2:14]([N:3]([CH2:1][CH3:2])[C:4](=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH:11]([Si:32]([CH3:34])([CH3:33])[CH3:31])[CH3:12])[CH3:15]

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 225866n,n,2-triethylbenzamideHCID 2724682Lithium diisopropylamideHCID 18522661Acetone cardice

Product 1

HCID 11425908HCID 11425908, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5.13 g (25 mmol) of N,N,2-triethylbenzamide in THF (50 mL) at -78° C. was added a solution of LDA (Aldrich 2.0M, 15.63 mL, 31.25 mmol). The solution was warmed to -10° C. with ice water over 1 hr, then cooled to -78° C. with dry ice-acetone. TMSCl (6.34 mL, 50 mmol) was added neat at -78° C. and then reaction brought to room temperature after 1 hr. The reaction was quenched with saturated NH4Cl and extracted with ether (2×100 mL), dried over MgSO4, stripped and the residue distilled in a Kugelrohr (130°-140° C., 0.65 mm) to obtain 6.51 g (94%) of N,N-diethyl-2-[1-(trimethylsilyl)ethyl]benzamide.

Workup

  1. customreaction
  2. customThe reaction was quenched with saturated NH4Cl
  3. extractionextracted with ether (2×100 mL)
  4. dry with materialdried over MgSO4
  5. distillationthe residue distilled in a Kugelrohr (130°-140° C., 0.65 mm)

Sources & evidence

ORD record
ord-6ba0c292d20a4778a0285ce387a96d61
Source dataset
uspto-grants-1996_10
Patent number
US05563163

Reaction notes

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