Reacción #1702074

ord-935790ee94ee465794ffa077fa2f1050

Ecuación de reacción

CC1(C)CCC(C)(C)c2cc3c(=O)ccoc3cc21
6,7,8,9-tetrahydro-6,6,9,9-tetramethyl-4H-naphtho[2,3-b]pyran-4-one
CC1(C)CCC(C)(C)c2cc3c(=O)ccoc3cc21
compound N
CC1(C)CCC(C)(C)c2cc3c(=O)ccoc3cc21
6,7,8,9-tetrahydro-6,6,9,9-tetramethyl-4H-naphtho[2,3-b]pyran-4-one
CO
methanol
CC1(C)CCC(C)(C)c2cc3c(cc21)OCCC3=O
2,3,6,7,8,9-hexahydro-6,6,9,9-tetramethyl-4H-naphtho[2,3-b]pyran-4-one

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    FiltraciónThe reaction solution was filtrated by celite
  2. 2
    Concentraciónthe filtrate was concentrated under reduced pressure
  3. 3
    OtroThe crude product was purified by silica gel chromatography

Procedimiento

The synthesis process is as set forth in the chemical reaction formula below. To 6,7,8,9-tetrahydro-6,6,9,9-tetramethyl-4H-naphtho[2,3-b]pyran-4-one (the above named compound N) (124 mg, 0.48 mmol) were added methanol (4.0 mL), ethyl acetate (4.0 mL) and 10% palladium on carbon (40 mg), followed by stirring under a hydrogen atmosphere at room temperature for 10 hours. The reaction solution was filtrated by celite, and the filtrate was concentrated under reduced pressure. The crude product was purified by silica gel chromatography using hexane/ethyl acetate (4/1 to 2/1) as an elution solvent. The yield was 80.0 mg (64%).

Fuente

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