Hydrochloric Acid → HCID 59191265, compound

HRID 1023973Notes

Reaction equation

HRID 1023973 reaction equation
C([O:3][C:4](=[O:30])[C:5](CC)(CC)[CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH3:23])=[CH:18][C:17]=2[OH:24])=[C:11]([F:25])[CH:10]=1)C.C1COCC1.C([O-])(O)=O.[Na+].[OH-].[Li+].Cl>>[CH2:22]([C:19]1[CH:20]=[CH:21][C:16]([O:15][C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:7][CH2:6][CH2:5][C:4]([OH:30])=[O:3])=[CH:10][C:11]=2[F:25])=[C:17]([OH:24])[CH:18]=1)[CH3:23]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 68546039HCID 68546039, compoundHCID 86639098HCID 86639098, compound

Product 1

HCID 59191265HCID 59191265, compoundYield 100%

Conditions

Temperature
60 °C

Procedure

To a solution of ethyl ethyl 4-[4-(4-Ethyl-2-hydroxy-phenoxy)-3-fluoro-phenoxy]-butyric acid ethyl ester (0.16 mmol; 58 mg), in a THF/water mixture (1/1; 1 mL) was added lithium hydroxide (0.64 mmol; 15 mg). The reaction was heated 1 hour at 60° C. After cooling to 0° C., the reaction was treated with concentrated HCl, and extracted with ethyl acetate (3*2 mL). Combinated organic phases were dried over Na2SO4 and concentrated in vacuo. The title compound (0.16 mmol; 54 mg; quantitative) was obtained as a clear oil, used without purification.

Workup

  1. temperatureAfter cooling to 0° C.
  2. extractionextracted with ethyl acetate (3*2 mL)
  3. dry with materialCombinated organic phases were dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2b6e1995512441ebb71b6015095b15d3
Source dataset
uspto-grants-2014_05
Patent number
US08722746B2

Reaction notes

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