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

HRID 238598Notes

Reaction equation

HRID 238598 reaction equation
[CH3:1][O:2][C:3](=[O:24])[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)[CH:6]=1>CO.[Pd]>[CH3:1][O:2][C:3](=[O:24])[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)[CH:6]=1

Participants

4

Reactant 1

HCID 59326591(4-Benzyloxy-6-fluoro-naphthalen-2-yl)-acetic acid methyl ester

Product 1

HCID 20335012(6-Fluoro-4-hydroxy-naphthalen-2-yl)-acetic acid methyl esterYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (4-benzyloxy-6-fluoro-naphthalen-2-yl)-acetic acid methyl ester (876 mg, 2.7 mmol) in methanol (20 mL) was added 10% palladium on carbon (132 mg). The resulting mixture was stirred vigorously under a hydrogen atmosphere (balloon) overnight and then filtered. The filtrate was concentrated in vacuo to give (6-fluoro-4-hydroxy-naphthalen-2-yl)-acetic acid methyl ester (601 mg, 95%) as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.69-7.76 (m, 2H), 7.30 (s, 1H), 7.22-7.26 (m, 1H), 6.82 (s, 1H), 3.74 (s, 3H), 3.72 (s, 2H).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-af84e06ba3ab4e8ab61ed61007bf6994
Source dataset
uspto-grants-2014_02
Patent number
US08642629B2

Reaction notes

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