HCID 58883454, compound → HCID 69074359, compound

HRID 1870031Notes

Reaction equation

HRID 1870031 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])=[C:13]([CH3:16])[CH:14]=2)[C:9]([CH3:26])([CH3:25])[CH2:8][CH:7]=1)=[O:5])[CH3:2]>C(O)C.[Pd].C(OCC)(=O)C>[CH2:1]([O:3][C:4]([CH:6]1[C:15]2[C:10](=[CH:11][C:12]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:19])[CH3:20])=[C:13]([CH3:16])[CH:14]=2)[C:9]([CH3:25])([CH3:26])[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 1

HCID 58883454HCID 58883454, compound2×

Product 1

HCID 69074359HCID 69074359, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 6-(tert-butyl-dimethyl-silanyloxy)-4,4,7-trimethyl-3,4-dihydronaphthalene-1-carboxylic acid ethyl ester (Intermediate 190, 0.95 g, 2.54 mmol) in ethanol was treated with a slurry of 5% palladium on carbon (0.3 g) in ethyl acetate (0.5 mL) and the resulting reaction mixture was stirred under an atmosphere of hydrogen overnight. The solids were filtered over a bed of celite and the filtrate was evaporated in vacuo to afford the title compound as a viscous oil (0.95 g, ˜100%).

Workup

  1. customthe resulting reaction mixture
  2. filtrationThe solids were filtered over a bed of celite
  3. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-2a79658292bb47e68e9833fb6d30960a
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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