Chlorotrimethylsilane → HCID 178487197, compound

HRID 1762583Notes

Reaction equation

HRID 1762583 reaction equation
C([Li])CCC.C(NC(C)C)(C)C.[CH3:13][O:14][C:15]1[CH:16]=[CH:17][C:18]2[CH:21]=[C:20]([CH2:22][N:23]3[CH2:28][CH2:27][C:26](=[O:29])[CH2:25][CH2:24]3)[C:19]=2[CH:30]=1.[CH3:31][Si:32]([CH3:35])([CH3:34])Cl>CCCCCC.O1CCCC1>[CH3:13][O:14][C:15]1[CH:16]=[CH:17][C:18]2[CH:21]=[C:20]([CH2:22][N:23]3[CH2:28][CH2:27][C:26]([O:29][Si:32]([CH3:35])([CH3:34])[CH3:31])=[CH:25][CH2:24]3)[C:19]=2[CH:30]=1

Participants

7

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 7912DiisopropylamineHCID 178418339ButyllithiumHCID 178487196HCID 178487196, compound

Product 1

HCID 178487197HCID 178487197, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Procedure

17.4 ml of n-butyllithium in hexane are added at 0°-5° to a solution of 2.81 g of diisopropylamine in 30 ml of dry tetrahydrofuran. The whole is stirred at room temperature for 30 minutes, is again cooled to -15° and a solution of 6.13 g (25 mmol) of 1-[(5-methoxybenzocyclobuten-1-yl)methyl]-piperidin-4-one in 30 ml of tetrahydrofuran is added. After 15 minutes, a solution of 3.05 g (28 mmol) of trimethylchlorosilane in 15 ml of tetrahydrofuran is added dropwise. The whole is stirred overnight at room temperature, filtered and concentrated to dryness by evaporation in vacuo. 1-[(5-methoxybenzocyclobuten-1-yl)methyl]-4-trimethylsilyloxy-1,2,5,6-tetrahydro-pyridine is thus obtained in the form of a light-yellow oil.

Workup

  1. temperatureis again cooled to -15°
  2. waitAfter 15 minutes
  3. stirringThe whole is stirred overnight at room temperature
  4. filtrationfiltered
  5. concentrationconcentrated to dryness by evaporation in vacuo

Sources & evidence

ORD record
ord-d196efec46f94d0e846f93b34f4fedd9
Source dataset
uspto-grants-1989_05
Patent number
US04833169

Reaction notes

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