Sodium Hydroxide → HCID 69801636, compound

HRID 984311Notes

Reaction equation

HRID 984311 reaction equation
C([O:3][C:4](=[O:33])[C@@H:5]([O:30][CH2:31][CH3:32])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14]/[CH:15]=[CH:16]/[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:18]=2)=[CH:9][CH:8]=1)C.[OH-].[Na+]>C(O)C>[CH2:31]([O:30][C@@H:5]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14]/[CH:15]=[CH:16]/[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:18]=2)=[CH:9][CH:8]=1)[C:4]([OH:33])=[O:3])[CH3:32]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69797612HCID 69797612, compound

Product 1

HCID 69801636HCID 69801636, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(E)-(S)-2-Ethoxy-3-{4-[3-(3-phenoxy-phenyl)-allyloxy]-phenyl}-propionic acid ethyl ester (example 25) (150 mg, 0.34 mmol) was dissolved in ethanol (7 mL) and sodium hydroxide (1N, 4.4 mL, 4.4 mmol) added. The mixture was heated slightly to obtain a clear solution and then stirred at room temperature for 1.5 h. The ethanol was evaporated in vacuo and the mixture acidified to pH 1 with 1N hydrochloric acid. The product was isolated by extraction with ethyl acetate (40 mL×2). The combined organic phases were dried (MgSO4), filtered and evaporated to give 130 mg (91%) of the title compound as an oil.

Workup

  1. temperatureThe mixture was heated slightly
  2. customto obtain a clear solution
  3. customThe ethanol was evaporated in vacuo
  4. customThe product was isolated by extraction with ethyl acetate (40 mL×2)
  5. dry with materialThe combined organic phases were dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-be0935bc319642fcb2483e1cf335441a
Source dataset
uspto-grants-2005_03
Patent number
US06867218B2

Reaction notes

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