HCID 18705088, compound → HCID 18705094, compound

HRID 2287453Notes

Reaction equation

HRID 2287453 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:8]2[O:13][CH:12]=[CH:11][C:10](=[O:14])[C:9]=2[CH:15]=1)([CH3:4])([CH3:3])[CH3:2]>CCOC(C)=O.[Pd]>[C:1]([C:5]1[CH:15]=[C:9]2[C:8](=[C:7]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:6]=1)[O:13][CH2:12][CH2:11][C:10]2=[O:14])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 18705088HCID 18705088, compound

Product 1

HCID 18705094HCID 18705094, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To 1.0 g (3.87 mmol) of 4H-6,8-di-t-butyl-benzopyran-4-one in 8 mL of EtOAc was added 200 mg of 10% Pd/C. The mixture was degassed, followed by addition of H2 gas and stirred under an H2 gas atmosphere for 2 h at RT. After filtration (celite), the product was concentrated and purified (SiO2 chromatography, 5% EtOAc-hexanes) to give 857 mg (3.29 mmol) of 32 as a white solid (85% yield): TLC (5% EtOAc-hex) Rf 0.7; 1H-NMR (CDCl3)δ 1.32 (s, 9H, CH3), 1.42 (s, 9H, CH3), 2.78 (t, J=6.0 Hz, 2H, CH2), 4.52 (t, J=6.0 Hz, 2H, CH2), 7.53 (d, J=2.4 Hz, 1H, Ar--H), 7.81 (d, J=2.4 Hz, 1H, Ar--H)

Workup

  1. customThe mixture was degassed
  2. additionfollowed by addition of H2 gas
  3. filtrationAfter filtration (celite)
  4. concentrationthe product was concentrated
  5. custompurified (SiO2 chromatography, 5% EtOAc-hexanes)

Sources & evidence

ORD record
ord-859959eabb0a4137a16a7114840be5e6
Source dataset
uspto-grants-2000_07
Patent number
US06083977

Reaction notes

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