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

HRID 238642Notes

Reaction equation

HRID 238642 reaction equation
[CH3:1][O:2][C:3](=[O:26])[CH2:4][C:5]1[C:14]([C:15]#[C:16][Si](C)(C)C)=[C:13]([O:21][C:22](=[O:24])[CH3:23])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:25])[CH:11]=2)[CH:6]=1.[F-].[K+]>CN(C)C=O.O>[CH3:1][O:2][C:3](=[O:26])[CH2:4][C:5]1[C:14]([C:15]#[CH:16])=[C:13]([O:21][C:22](=[O:24])[CH3:23])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:25])[CH:11]=2)[CH:6]=1

Participants

5

Reactant 2

HCID 522689Potassium FluorideHCID 59326569(4-Acetoxy-6-fluoro-3-trimethylsilanylethynyl-naphthalen-2-yl)-acetic acid methyl ester

Product 1

HCID 59326564(4-Acetoxy-3-ethynyl-6-fluoro-naphthalen-2-yl)-acetic acid methyl esterYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

To a solution of (4-acetoxy-6-fluoro-3-trimethylsilanylethynyl-naphthalen-2-yl)-acetic acid methyl ester (200 mg, 0.538 mmol) in N,N-dimethylformamide and water (6 mL, v/v=150:1), was added potassium fluoride (156 mg, 2.7 mmol). The resulting mixture was stirred at room temperature for 4 hours, then poured into water (10 mL), and extracted with ethyl acetate (10 mL×3). The organic layers were combined, washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash column (elution with 10% ethyl acetate in petroleum ether) to afford (4-acetoxy-3-ethynyl-6-fluoro-naphthalen-2-yl)-acetic acid methyl ester (153 mg, 95%) as a light yellow solid.

Workup

  1. extractionextracted with ethyl acetate (10 mL×3)
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column (elution with 10% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-d17578ecb34046168a77be6a547b83f3
Source dataset
uspto-grants-2014_02
Patent number
US08642629B2

Reaction notes

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