6-Fluoronaphthalene-1-carboxylic acid → HCID 14987239, compound

HRID 1091155Notes

Reaction equation

HRID 1091155 reaction equation
[CH3:1][Li].[F:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:10]([C:14]([OH:16])=O)=[CH:9][CH:8]=[CH:7]2>C1COCC1>[F:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:10]([C:14](=[O:16])[CH3:1])=[CH:9][CH:8]=[CH:7]2

Participants

4

Reactant 2

HCID 145813856-Fluoronaphthalene-1-carboxylic acidHCID 178418348HCID 178418348, compound

Product 1

HCID 14987239HCID 14987239, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl lithium (1.59M solution in ether; 4.2 ml) was added dropwise to a stirred solution of 6-fluoro-1-naphthalene carboxylic acid (640 mg) in dry THF (10 ml) at -78° under nitrogen. The solution was stirred at -78° for 2 h and was slowly allowed to warm to -15°. The solution was quenched with saturated aqueous ammonium chloride (1 ml) and partitioned between 2N sodium hydroxide (25 ml) and ethyl acetate (25 ml). The organic phase was dried and evaporated to give the title compound (404 mg) as an oil, t.l.c. (System B, 1:6) Rf 0.2.

Workup

  1. temperatureto warm to -15°
  2. customThe solution was quenched with saturated aqueous ammonium chloride (1 ml)
  3. custompartitioned between 2N sodium hydroxide (25 ml) and ethyl acetate (25 ml)
  4. customThe organic phase was dried
  5. customevaporated

Sources & evidence

ORD record
ord-c7288cab9608422a998c10045947a0d1
Source dataset
uspto-grants-1992_01
Patent number
US05084474

Reaction notes

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