(4-Acetoxy-3-ethynyl-6-fluoro-naphthalen-2-yl)-acetic acid methyl ester → (4-Acetoxy-3-ethyl-6-fluoro-naphthalen-2-yl)acetic acid methyl ester

HRID 238647Notes

Reaction equation

HRID 238647 reaction equation
[CH3:1][O:2][C:3](=[O:22])[CH2:4][C:5]1[C:14]([C:15]#[CH:16])=[C:13]([O:17][C:18](=[O:20])[CH3:19])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:21])[CH:11]=2)[CH:6]=1.[H][H]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:22])[CH2:4][C:5]1[C:14]([CH2:15][CH3:16])=[C:13]([O:17][C:18](=[O:20])[CH3:19])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:21])[CH:11]=2)[CH:6]=1

Participants

5

Reactant 2

HCID 59326564(4-Acetoxy-3-ethynyl-6-fluoro-naphthalen-2-yl)-acetic acid methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 59326550(4-Acetoxy-3-ethyl-6-fluoro-naphthalen-2-yl)acetic acid methyl esterYield 98.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (4-acetoxy-3-ethynyl-6-fluoro-naphthalen-2-yl)-acetic acid methyl ester (50 mg) in methanol was added 10% palladium on carbon (10 mg). The resulting mixture was hydrogenated under 40 psi of hydrogen for 2 hours and filtered. The filtrate was concentrated in vacuo to afford (4-acetoxy-3-ethyl-6-fluoro-naphthalen-2-yl)acetic acid methyl ester (50 mg) as a colorless oil.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-96baf2beaa0b411dad6a853321e885c7
Source dataset
uspto-grants-2014_02
Patent number
US08642629B2

Reaction notes

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