(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 1644741Notes

Reaction equation

HRID 1644741 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]>C(O)C.[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 92.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

A round-bottom flask was charged with (4-benzyloxy-6-fluoro-3-methyl-naphthalen-2-yl)-acetic acid methyl ester (11.7 g, 34.58 mmol) in ethanol (350 mL). Some heating was required in order to dissolve all of the starting material in ethanol. A full spatula scoop of 10% palladium on carbon was added into the reaction flask. The reaction mixture was stirred under hydrogen gas at atmospheric pressure overnight at room temperature. After this time, it appeared that approximately 750 mL hydrogen gas had been consumed, and TLC (1:3 ethyl acetate, hexanes) indicated that the starting material had been consumed. The reaction mixture was filtered through a bed of celite. The filtrate was concentrated to afford 7.91 g (92%) of (6-fluoro-4-hydroxy-3-methyl-naphthalen-2-yl)-acetic acid methyl ester, which was used in the next step without further purification. MS (ES−) cald. for C14H13FO3 [(M−H)−] 247, obsd. 247.1.

Workup

  1. customhad been consumed
  2. customhad been consumed
  3. filtrationThe reaction mixture was filtered through a bed of celite
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-958d391e86d24a419fc56c9b199141b9
Source dataset
uspto-grants-2012_02
Patent number
US08124629B2

Reaction notes

Loading…