Ethyl acetate hexane → (6-Fluoro-4-hydroxy-naphthalen-2-yl)-acetic acid methyl ester

HRID 2363811Notes

Reaction equation

HRID 2363811 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.[H][H].C(OCC)(=O)C.CCCCCC>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

6

Reactant 3

HCID 21226206Ethyl acetate hexaneHCID 59326591(4-Benzyloxy-6-fluoro-naphthalen-2-yl)-acetic acid methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 20335012(6-Fluoro-4-hydroxy-naphthalen-2-yl)-acetic acid methyl esterYield 76.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of (4-benzyloxy-6-fluoro-naphthalen-2-yl)-acetic acid methyl ester (18.5 g, 57.0 mmol) in methanol (200 mL) was added 10% palladium on carbon (2.78 g). The resulting mixture was vigorously stirred under a balloon of hydrogen overnight. The reaction mixture was filtered through celite. The filtrate was concentrated in vacuo to obtain a crude product. Silica gel chromatography (10% ethyl acetate-hexane) afforded (6-fluoro-4-hydroxy-naphthalen-2-yl)-acetic acid methyl ester (10.24 g, 76%) as a white solid. MS cald. for C13H12FO3 [(M+H)+]: 235, obsd. 235.2.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationThe filtrate was concentrated in vacuo
  3. customto obtain a crude product

Sources & evidence

ORD record
ord-29381af57eea46d3852e94419ce1b767
Source dataset
uspto-grants-2014_04
Patent number
US08691993B2

Reaction notes

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