(4-Benzyloxy-6-fluoro-3-methyl-naphthalen-2-yl)-acetic acid methyl ester → (6-Fluoro-4-hydroxy-3-methyl-naphthalen-2-yl)-acetic acid methyl ester

HRID 238605Notes

Reaction equation

HRID 238605 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH2:4][C:5]1[C:14]([CH3:15])=[C:13]([O:16]CC2C=CC=CC=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:24])[CH:11]=2)[CH:6]=1>CO.[Pd]>[CH3:1][O:2][C:3](=[O:25])[CH2:4][C:5]1[C:14]([CH3:15])=[C:13]([OH:16])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:24])[CH:11]=2)[CH:6]=1

Participants

4

Reactant 1

HCID 59326535(4-Benzyloxy-6-fluoro-3-methyl-naphthalen-2-yl)-acetic acid methyl ester

Product 1

HCID 59326522(6-Fluoro-4-hydroxy-3-methyl-naphthalen-2-yl)-acetic acid methyl esterYield 98.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (4-benzyloxy-6-fluoro-3-methyl-naphthalen-2-yl)-acetic acid methyl ester (3.4 g, 10.0 mmol) in methanol (50 mL) was added 10% palladium on carbon (0.5 g). The resulting mixture was vigorously stirred under a hydrogen (balloon) atmosphere overnight. The filtrate was concentrated in vacuo to give (6-fluoro-4-hydroxy-3-methyl-naphthalen-2-yl)-acetic acid methyl ester (2.44 g, 98%) as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.69-7.74 (m, 2H), 7.34 (s, 1H), 7.21 (td, J=2.4, 8.4 Hz, 1H), 5.16 (s, 1H), 3.82 (s, 2H), 3.74 (s, 3H), 2.35 (s, 3H); MS cald. for C14H13FO3 248, obsd. (ESI+) [(M+H)+] 249.

Workup

  1. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-ccc12d78ade2466f8694aed4a56037cc
Source dataset
uspto-grants-2014_02
Patent number
US08642629B2

Reaction notes

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