Reaction #1702074

Reaction equation

6,7,8,9-tetrahydro-6,6,9,9-tetramethyl-4H-naphtho[2,3-b]pyran-4-one

compound N

6,7,8,9-tetrahydro-6,6,9,9-tetramethyl-4H-naphtho[2,3-b]pyran-4-one

methanol

→

2,3,6,7,8,9-hexahydro-6,6,9,9-tetramethyl-4H-naphtho[2,3-b]pyran-4-one

Solvents

ethyl acetate

Conditions

Workup

1. 1
   FiltrationThe reaction solution was filtrated by celite
2. 2
   Concentrationthe filtrate was concentrated under reduced pressure
3. 3
   OtherThe crude product was purified by silica gel chromatography

Procedure

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%).

Source