N,N-Dimethylformamide--water (1/1) → 3-(2-Fluoro-3-methoxyphenyl)pentanoic acid

HRID 1662504Notes

Reaction equation

HRID 1662504 reaction equation
[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:10]([CH:13]1C(=O)OC(C)(C)[O:15][C:14]1=[O:22])[CH2:11][CH3:12].CN(C=O)C.O>CCOCC>[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:10]([CH2:11][CH3:12])[CH2:13][C:14]([OH:22])=[O:15]

Participants

4

Reactant 2

HCID 21962138N,N-Dimethylformamide--water (1/1)HCID 57705536HCID 57705536, compound

Product 1

HCID 577061663-(2-Fluoro-3-methoxyphenyl)pentanoic acidYield 91.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
90 °C

Procedure

A 500 mL round bottom flask was charged with 5-(1-(2-fluoro-3-methoxyphenyl)propyl)-2,2-dimethyl-1,3-dioxane-4,6-dione 77.C (5.17 g, 16.7 mmol) and 10:1 DMF/water (80 mL). The pale yellow solution was stirred overnight at 90° C., cooled to room temperature, and diluted with ether. The combined organic layers were washed with water and brine, dried (MgSO4), and concentrated to afford 3-(2-fluoro-3-methoxyphenyl)pentanoic acid 77.D (3.44 g, 91.3% yield) as a yellow oil. The crude product was used without further purification.

Workup

  1. temperaturecooled to room temperature
  2. washThe combined organic layers were washed with water and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-255054c50813443e91e3987865712668
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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