Sodium Hydroxide → 1-(5-Fluoro-1-naphthalenyl)ethanone

HRID 2051568Notes

Reaction equation

HRID 2051568 reaction equation
[CH3:1][Li].[F:3][C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]([OH:16])=O.[OH-].[Na+]>C1COCC1>[F:3][C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14](=[O:16])[CH3:1]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 149872365-Fluoronaphthalene-1-carboxylic acidHCID 178418348HCID 178418348, compound

Product 1

HCID 149872371-(5-Fluoro-1-naphthalenyl)ethanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl lithium (1.4M solution in ether; 6.6ml) was added dropwise to a stirred solution of 5-fluoro-1-naphthalene carboxylic acid (870mg) in dry THF (15 ml) at -78° under nitrogen. The reaction mixture was allowed to warm to room temperature over 2 h and was treated with 2N sodium hydroxide (60 ml). The mixture was extracted with ether (2×30 ml), and the combined, dried organic extracts were evaporated to give the title compound (865 mg) as an oil, t.l.c. (System B, 1:6) Rf 0.3

Workup

  1. extractionThe mixture was extracted with ether (2×30 ml)
  2. customdried organic extracts were evaporated

Sources & evidence

ORD record
ord-df6c2521fa4241e984d4846c844c631e
Source dataset
uspto-grants-1991_05
Patent number
US05019586

Reaction notes

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