p-Toluidine → HCID 178426070, compound

HRID 1531468Notes

Reaction equation

HRID 1531468 reaction equation
[H-].[K+:2].[H-].[Na+].CC1C=CC(N)=CC=1.[CH3:13][C:14]1[CH2:18][C:17]([CH3:19])=[C:16]([CH3:20])[C:15]=1[CH3:21]>O1CCCC1>[CH3:13][C:14]1[CH:18]([K:2])[C:17]([CH3:19])=[C:16]([CH3:20])[C:15]=1[CH3:21]

Participants

6

Reactant 4

HCID 7813p-ToluidineHCID 24758Sodium hydrideHCID 82127Potassium hydrideHCID 1381631,2,3,4-Tetramethylcyclopentadiene

Product 1

HCID 178426070HCID 178426070, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

Potassium hydride (containing mineral oil; the content of sodium hydride: 35%) (3.00 g) was suspended in tetrahydrofuran (18 ml), and then 4-methylaniline (0.056 g) was dropwise added to the suspension at 10° C., followed by stirring for 10 minutes. Thereafter, the solution of tetramethylcyclopentadiene (1.22 g) dissolved in tetrahydrofuran (6 ml) was dropwise added to the suspension, and heated to 25° C., followed by stirring for one hour. Thus, tetramethylcyclopentadienylpotassium was obtained. To this solution, the solution of (2-allyloxy-3-tert.-butyl-5-methylphenyl)chlorodimethylsilane (3.99 g; purity: 70.7%; pure compound: 2.82 g) dissolved in tetrahydrofuran (3 ml) was dropwise added, followed by stirring for one hour.

Workup

  1. additionwas dropwise added to the suspension
  2. stirringby stirring for one hour

Sources & evidence

ORD record
ord-50115ddca2774080b32a4f2dcac5599f
Source dataset
uspto-grants-2001_03
Patent number
US06197990B1

Reaction notes

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