Aniline → HCID 178426071, compound

HRID 1531467Notes

Reaction equation

HRID 1531467 reaction equation
[H-].[Na+:2].NC1C=CC=CC=1.[CH3:10][C:11]1[CH2:15][C:14]([CH3:16])=[C:13]([CH3:17])[C:12]=1[CH3:18]>O1CCCC1>[CH3:10][C:11]1[CH:15]([Na:2])[C:14]([CH3:16])=[C:13]([CH3:17])[C:12]=1[CH3:18]

Participants

5

Reactant 3

HCID 6115AnilineHCID 24758Sodium hydride2×HCID 1381631,2,3,4-Tetramethylcyclopentadiene

Product 1

HCID 178426071HCID 178426071, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Sodium hydride (containing mineral oil; the content of sodium hydride: 60 wt. %) (0.60 g) was suspended in tetrahydrofuran (6.91 g), and then aniline (0.047 g) was dropwise added to the suspension at 25° C. After heating to 50° C., the suspension was stirred for 10 minutes. Thereafter, tetramethylcyclopentadiene (1.22 g) was dropwise added to the suspension while maintaining the suspension at 50° C., followed by stirring for one hour. Thus, tetramethylcyclopentadienylsodium was obtained. After cooling the above solution to 20° C., the solution of (2-allyloxy-3-tert.-butyl-5-methylphenyl)chlorodimethylsilane (3.86 g; purity: 73%; pure compound: 2.82 g) in toluene was dropwise added to the above solution, followed by stirring for 2 hours.

Workup

  1. temperaturewhile maintaining the suspension at 50° C.
  2. stirringby stirring for one hour

Sources & evidence

ORD record
ord-3853cc7a5e8543f8aa75811a5450f24b
Source dataset
uspto-grants-2001_03
Patent number
US06197990B1

Reaction notes

Loading…