Sodium Hydroxide → (E)-(S)-3-{4-[3-(4-bromophenyl)-but-2-enyloxy]-phenyl}-2-ethoxy-propionic acid

HRID 984315Notes

Reaction equation

HRID 984315 reaction equation
[OH-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7](/[C:10](/[CH3:30])=[CH:11]/[CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][C@H:21]([O:27][CH2:28][CH3:29])[C:22]([O:24]CC)=[O:23])=[CH:16][CH:15]=2)=[CH:6][CH:5]=1>C(O)C>[Br:3][C:4]1[CH:5]=[CH:6][C:7](/[C:10](/[CH3:30])=[CH:11]/[CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][C@H:21]([O:27][CH2:28][CH3:29])[C:22]([OH:24])=[O:23])=[CH:16][CH:15]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86589946(E)-(S)-ethyl 3-{4-[3-(4-bromophenyl)-but-2-enyloxy]-phenyl}-2-ethoxy-propionate

Product 1

HCID 69800665(E)-(S)-3-{4-[3-(4-bromophenyl)-but-2-enyloxy]-phenyl}-2-ethoxy-propionic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium hydroxide (1M, 1.10 ml, 1.10 mmol) was added to a solution of (E)-(S)-ethyl 3-{4-[3-(4-bromophenyl)-but-2-enyloxy]-phenyl}-2-ethoxy-propionate (example 50) (0.245 g, 0.548 mmol) in ethanol (10 ml) and the mixture stirred at room temperature for 18 h. The resulting mixture was partitioned between water (50 ml) and ethyl acetate (50 ml) and the aqueous layer acidified to pH1 by addition of 1N HCl. The aqueous layer was separated and further extracted with ethyl acetate (2×50 ml). The combined organic layers were washed with brine, dried (MgSO4), evaporated and vacuum dried at 40° C. for 18 h, to give (E)-(S)-3-{4-[3-(4-bromophenyl)-but-2-enyloxy]-phenyl}-2-ethoxy-propionic acid as a colourless gum which contained 0.1 molar equivalents of ethyl acetate; 0.22 g (96%).

Workup

  1. customThe resulting mixture was partitioned between water (50 ml) and ethyl acetate (50 ml)
  2. additionthe aqueous layer acidified to pH1 by addition of 1N HCl
  3. customThe aqueous layer was separated
  4. extractionfurther extracted with ethyl acetate (2×50 ml)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customvacuum dried at 40° C. for 18 h

Sources & evidence

ORD record
ord-5a828524eabe49bbb2053ab568767aed
Source dataset
uspto-grants-2005_03
Patent number
US06867218B2

Reaction notes

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