HCID 54227728, compound → HCID 19348492, compound

HRID 1637519Notes

Reaction equation

HRID 1637519 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:12]([O:28][CH3:29])[CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H][H]>C(OCC)(=O)C.[Pd]>[Si:1]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]([CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:12]([O:28][CH3:29])[CH:11]=1)([C:4]([CH3:5])([CH3:7])[CH3:6])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 54227728HCID 54227728, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19348492HCID 19348492, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 27.92 g (66.4 mmol) of ethyl 3-(4-t-butyldimethylsilyloxymethyl-2-methoxyphenyl)-2-octenoate [prepared as described in step (iii) above] in 200 ml of ethyl acetate was vigorously stirred for 8 hours in the presence of 1.58 g of 10% palladium-on-charcoal in a stream of hydrogen. At the end of this time, the catalyst was filtered off, and the filtrate was concentrated by evaporation under reduced pressure, to give 28.25 g (a quantitative yield) of the title compound as an oily substance.

Workup

  1. filtrationAt the end of this time, the catalyst was filtered off
  2. concentrationthe filtrate was concentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-d8c52055f4ec4b9193e8f209f25a07b5
Source dataset
uspto-grants-2000_03
Patent number
US06040339

Reaction notes

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