Chlorotrimethylsilane → HCID 12918300, compound

HRID 1380483Notes

Reaction equation

HRID 1380483 reaction equation
C([Mg]Br)C.[CH:5](=[N:12][CH2:13][C:14]#[CH:15])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:16][Si:17](Cl)([CH3:19])[CH3:18]>O1CCCC1.[Cl-].[Na+].O>[CH:5](=[N:12][CH2:13][C:14]#[C:15][Si:17]([CH3:19])([CH3:18])[CH3:16])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 4172560N-BENZYLIDENE-2-PROPYNYLAMINEHCID 178418443HCID 178418443, compound

Product 1

HCID 12918300HCID 12918300, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

10 g of ethyl magnesium bromide was added over 30 minutes to a stirred solution of 10.2 g of 1A in 100 ml of tetrahydrofuran at 0° C. The resulting mixture was stirred at that temperature for 30 minutes, then a solution of 7.75 g of trimethylsilyl chloride in 30 ml of tetrahydrofuran was added over 30 minutes. The mixture then was stirred at 0° C. for 90 minutes, treated with brine, dried (MgSO4) and the solvent was evaporated. The residue was distilled at 85°-90° C., 0.3 Torr., to give N-benzylidene-3-(trimethylsilyl)-2-propyn-1-amine (1B), as a water-white oil.

Workup

  1. stirringThe mixture then was stirred at 0° C. for 90 minutes
  2. dry with materialdried (MgSO4)
  3. customthe solvent was evaporated
  4. distillationThe residue was distilled at 85°-90° C.

Sources & evidence

ORD record
ord-99b4298051e540bfabf2fd0e49edfc43
Source dataset
uspto-grants-1986_04
Patent number
US04582529

Reaction notes

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