Sodium Hydroxide → HCID 59028779, compound

HRID 1715056Notes

Reaction equation

HRID 1715056 reaction equation
C([O:3][C:4](=[O:27])[CH2:5][CH2:6][C:7]1[C:16]2[C:11](=[CH:12][C:13]([S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=3)(=[O:19])=[O:18])=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1)C.[OH-].[Na+]>C(O)C.C1(C)C=CC=CC=1>[F:26][C:22]1[CH:21]=[C:20]([S:17]([C:13]2[CH:12]=[C:11]3[C:16](=[CH:15][CH:14]=2)[C:7]([CH2:6][CH2:5][C:4]([OH:27])=[O:3])=[CH:8][CH:9]=[CH:10]3)(=[O:18])=[O:19])[CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 59028778HCID 59028778, compound

Product 1

HCID 59028779HCID 59028779, compoundYield 86.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

3-[6-(3-Fluoro-benzenesulfonyl)-naphthalen-1-yl]-propionic acid ethyl ester (2.0 g) was dissolved in 25 mL ethanol, and 10 mL of 25% aqueous NaOH was added. The reaction mixture was heated to reflux for one hour, then cooled to room temperature. The ethanol was removed under reduced pressure, and the liquid residue was acidified by addition of 10% aqueous HCl. The mixture was extracted with EtOAc, and the combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure to give a crude oil. The oil was dissolved in warm toluene and insolubles were removed by filtration. The filtrate was concentrated under reduced pressure to give 1.6 g of 3-[6-(3-fluoro-benzenesulfonyl)-naphthalen-1-yl]-propionic acid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for one hour
  3. customThe ethanol was removed under reduced pressure
  4. additionthe liquid residue was acidified by addition of 10% aqueous HCl
  5. extractionThe mixture was extracted with EtOAc
  6. dry with materialthe combined organic layers were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto give a crude oil
  10. custominsolubles were removed by filtration
  11. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-cc53eff756fb444ca3b4cdf29e10a21a
Source dataset
uspto-grants-2010_09
Patent number
US07799797B2

Reaction notes

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