Potassium Hydroxide → (S)-2-((R)-2-(4-fluorophenyl)-2-hydroxyethyl)hexanoic acid

HRID 1643271Notes

Reaction equation

HRID 1643271 reaction equation
[CH2:1]([C@H:5]1[CH2:9][C@H:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[O:7][C:6]1=[O:17])[CH2:2][CH2:3][CH3:4].[OH-:18].[K+]>O1CCOCC1>[F:16][C:13]1[CH:14]=[CH:15][C:10]([C@H:8]([OH:7])[CH2:9][C@H:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:6]([OH:17])=[O:18])=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 59568766(3S,5R)-3-butyl-5-(4-fluorophenyl)dihydrofuran-2(3H)-one

Product 1

HCID 59568771(S)-2-((R)-2-(4-fluorophenyl)-2-hydroxyethyl)hexanoic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To the solution of (3S,5R)-3-butyl-5-(4-fluorophenyl)dihydrofuran-2(3H)-one (94.0 mg, 0.40 mmol) in 5 mL dioxane was added 5 mL aqueous 5% KOH at 25° C. After being stirred for 30 min at room temperature the reaction was quenched by the addition of 6 mL of 1M aqueous HCl. The mixture was extracted ethyl acetate (2×10 mL) and the combined organic layers were washed with brine (2×10 mL) before being concentrated under reduced pressure. The crude product was used directly in the next reaction without further purification.

Workup

  1. customwas quenched by the addition of 6 mL of 1M aqueous HCl
  2. extractionThe mixture was extracted ethyl acetate (2×10 mL)
  3. washthe combined organic layers were washed with brine (2×10 mL)
  4. concentrationbefore being concentrated under reduced pressure
  5. customThe crude product was used directly in the next reaction without further purification

Sources & evidence

ORD record
ord-4fc98081ff254165b5e20872b785e08a
Source dataset
uspto-grants-2012_02
Patent number
US08119692B2

Reaction notes

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