Methanol → HCID 10445237, compound

HRID 1614892Notes

Reaction equation

HRID 1614892 reaction equation
[CH3:1][C:2]1([CH3:19])[CH2:16][CH2:15][C:14]([CH3:18])([CH3:17])[C:13]2[C:3]1=[CH:4][C:5]1[C:10](=[O:11])[CH:9]=[CH:8][O:7][C:6]=1[CH:12]=2.CO>[Pd].C(OCC)(=O)C>[CH3:1][C:2]1([CH3:19])[CH2:16][CH2:15][C:14]([CH3:18])([CH3:17])[C:13]2[C:3]1=[CH:4][C:5]1[C:10](=[O:11])[CH2:9][CH2:8][O:7][C:6]=1[CH:12]=2

Participants

5

Reactant 2

HCID 887MethanolHCID 15187582HCID 15187582, compound2×

Product 1

HCID 10445237HCID 10445237, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

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%).

Workup

  1. filtrationThe reaction solution was filtrated by celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-935790ee94ee465794ffa077fa2f1050
Source dataset
uspto-grants-2014_07
Patent number
US08765719B2

Reaction notes

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