3-(2-t-Butyldimethylsilyloxylmethylnaphthalen-6-yl)acrylic acid methyl ester → 3-(6-t-butyldimethylsilyloxymethylnaphthalen-2-yl)propionic Acid Methyl Ester

HRID 1173987Notes

Reaction equation

HRID 1173987 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH:4]=[CH:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH:12]=[C:11]([CH2:16][O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH:10]=[CH:9]2>C1C=CC=CC=1.[Pd]>[CH3:1][O:2][C:3](=[O:25])[CH2:4][CH2:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH2:16][O:17][Si:18]([C:21]([CH3:23])([CH3:22])[CH3:24])([CH3:19])[CH3:20])[CH:12]=2)[CH:7]=1

Participants

4

Reactant 1

HCID 669418513-(2-t-Butyldimethylsilyloxylmethylnaphthalen-6-yl)acrylic acid methyl ester

Product 1

HCID 669415313-(6-t-butyldimethylsilyloxymethylnaphthalen-2-yl)propionic Acid Methyl EsterYield 102.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 241BenzeneSolvent

Procedure

The compound (2.54 g) obtained in Example 121-4 was dissolved in anhydrous benzene (80 ml) and added with palladium black, followed by stirring at room temperature for 1 hour under a nitrogen atmosphere. After completion of the reaction, the solution was filtrated through Celite. Then, the solvent was distilled off, thereby obtaining the subject compound (2.62 g) as a white solid.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe solution was filtrated through Celite
  3. distillationThen, the solvent was distilled off

Sources & evidence

ORD record
ord-0f649f17d5574364b5fe4ead5762151e
Source dataset
uspto-grants-2010_11
Patent number
US07833991B2

Reaction notes

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