(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 1261431Notes

Reaction equation

HRID 1261431 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.[H][H]>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

5

Reactant 2

HCID 59326535(4-Benzyloxy-6-fluoro-3-methyl-naphthalen-2-yl)-acetic acid methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 59326522(6-Fluoro-4-hydroxy-3-methyl-naphthalen-2-yl)-acetic acid methyl esterYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of (4-benzyloxy-6-fluoro-3-methyl-naphthalen-2-yl)-acetic acid methyl ester (15.8 g, 46.7 mmol) in MeOH (150 mL) was added 10% palladium on carbon (2.4 g). The resulting mixture was vigorously stirred under a balloon of hydrogen overnight. The reaction mixture was filtered through celite. The filtrate was concentrated to give the crude product, which was purified by silica gel chromatography (10% ethyl acetate in hexanes) to yield (6-fluoro-4-hydroxy-3-methyl-naphthalen-2-yl)-acetic acid methyl ester (9.5 g, 83%) as a white solid. MS cald. for C14H13FO3 [(M+H)+] 249, obsd. 249.1.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationThe filtrate was concentrated
  3. customto give the crude product, which
  4. customwas purified by silica gel chromatography (10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-27e8408b56e54f16a6910e43903074ba
Source dataset
uspto-grants-2013_06
Patent number
US08470884B2

Reaction notes

Loading…