Reacción #1702069

ord-6176243e874449c1aced6cbc468c3be3

Ecuación de reacción

CC1(C)CCC(C)(C)c2ccccc21
5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene
ClCCl
dichloromethane
[Al+3].[Cl-].[Cl-].[Cl-]
aluminum chloride
CC(C)C(=O)Cl
isobutyryl chloride
CC(C)C(=O)c1ccc2c(c1)C(C)(C)CCC2(C)C
5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl isopropyl ketone

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Extracciónextracted by ethyl acetate
  2. 2
    LavadoThe organic layer was washed by water
  3. 3
    Secadoa saturated sodium hydrogen carbonate aq. solution, and a saturated saline solution, dried over magnesium sulfate
  4. 4
    Concentraciónconcentrated under reduced pressure
  5. 5
    OtroThe crude product was purified by silica gel chromatography

Procedimiento

The synthesis process is as set forth in the chemical reaction formula below. To 5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene (188 mg, 1.00 mmol) were added anhydrous dichloromethane (1 mL), aluminum chloride (140 mg, 1.05 mmol), and isobutyryl chloride (112 mg, 1.05 mmol) followed by stirring at room temperature for 3 hours. The reaction solution was poured into cold water and extracted by ethyl acetate. The organic layer was washed by water, a saturated sodium hydrogen carbonate aq. solution, and a saturated saline solution, dried over magnesium sulfate, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography using hexane/ethyl acetate (20/1) as an elution solvent. The yield was 97.4 mg (38%).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08765719B2uspto-grants-2014_07