(4-Benzyloxy-6-fluoro-1-methyl-naphthalen-2-yl)-acetic acid methyl ester → (6-Fluoro-4-hydroxy-1-methyl-naphthalen-2-yl)acetic acid methyl ester

HRID 238623Notes

Reaction equation

HRID 238623 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH2:4][C:5]1[CH:14]=[C:13]([O:15]CC2C=CC=CC=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:23])[CH:11]=2)[C:6]=1[CH3:24]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:25])[CH2:4][C:5]1[CH:14]=[C:13]([OH:15])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:23])[CH:11]=2)[C:6]=1[CH3:24]

Participants

4

Reactant 1

HCID 59326512(4-Benzyloxy-6-fluoro-1-methyl-naphthalen-2-yl)-acetic acid methyl ester

Product 1

HCID 59326584(6-Fluoro-4-hydroxy-1-methyl-naphthalen-2-yl)acetic acid methyl esterYield 81.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (4-benzyloxy-6-fluoro-1-methyl-naphthalen-2-yl)-acetic acid methyl ester (50 mg) in methanol was added 10% palladium on carbon (10 mg). After being stirred at room temperature under a hydrogen atmosphere overnight, the resulting mixture was filtered. The filtrate was concentrated in vacuo to afford (6-fluoro-4-hydroxy-1-methyl-naphthalen-2-yl)-acetic acid methyl ester (30 mg) as a white solid.

Workup

  1. filtrationthe resulting mixture was filtered
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-99229b644acb4b0ba1cf1d5d2758c087
Source dataset
uspto-grants-2014_02
Patent number
US08642629B2

Reaction notes

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