Ethanol → (E)-(S)-3-[4-(3-biphenyl-4-yl-but-2-enyloxy)-phenyl]-2-ethoxy-propionic acid

HRID 413933Notes

Reaction equation

HRID 413933 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:31])[C@@H:7]([O:28][CH2:29][CH3:30])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16]/[CH:17]=[C:18](/[CH3:27])\[C:19]#CC2C=CC=CC=2)=[CH:11][CH:10]=1)C.[CH2:32](O)[CH3:33]>>[C:8]1([C:33]2[CH:32]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:9]=[CH:10][C:19](/[C:18](/[CH3:27])=[CH:17]/[CH2:16][O:15][C:12]2[CH:11]=[CH:10][C:9]([CH2:8][C@H:7]([O:28][CH2:29][CH3:30])[C:6]([OH:5])=[O:31])=[CH:14][CH:13]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 86583976(Z)-(S)-2-ethoxy-3-[4-(3-methyl-5-phenyl-pent-2-en-4-ynyloxy)-phenyl]-propionic acid ethyl ester

Product 1

HCID 10093355(E)-(S)-3-[4-(3-biphenyl-4-yl-but-2-enyloxy)-phenyl]-2-ethoxy-propionic acid

Conditions

Temperature
70 °C

Procedure

Sodium hydroxide (1N, 1.25 mL, 1.25 mmol) was added to a solution of (Z)-(S)-2-ethoxy-3-[4-(3-methyl-5-phenyl-pent-2-en-4-ynyloxy)-phenyl]-acid ethyl ester (example 3) (0.246 g, 0.627 mmol) in ethanol (20 mL) and the mixture stirred at 70° C. for 2.5 h. After cooling to room temperature the resulting mixture was partitioned between water (50 mL) and ethyl acetate (50 mL). The aqueous phase was collected, acidified with 1N hydrochloric acid (5 mL) and extracted into ethyl acetate (100 mL). The organic phase was washed with brine, dried (Na2SO4) and evaporated to give (E)-(S)-3-[4-(3-biphenyl-4-yl-but-2-enyloxy)-phenyl]-2-ethoxy-propionic acid as an oil; 0.150 g (66%).

Workup

  1. temperatureAfter cooling to room temperature the resulting mixture
  2. customwas partitioned between water (50 mL) and ethyl acetate (50 mL)
  3. customThe aqueous phase was collected
  4. extractionextracted into ethyl acetate (100 mL)
  5. washThe organic phase was washed with brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated

Sources & evidence

ORD record
ord-740756a8548a47d6877fac2f8f66934a
Source dataset
uspto-grants-2003_05
Patent number
US06569901B2

Reaction notes

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