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

HRID 984305Notes

Reaction equation

[OH-].[Na+].[C:3]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:8]=[CH:7][C:6](/[C:9](/[CH3:29])=[CH:10]/[CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][C@H:20]([O:26][CH2:27][CH3:28])[C:21]([O:23]CC)=[O:22])=[CH:15][CH:14]=2)=[CH:5][CH:4]=1>C(O)C>[C:3]1([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:4]=[CH:5][C:6](/[C:9](/[CH3:29])=[CH:10]/[CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][C@H:20]([O:26][CH2:27][CH3:28])[C:21]([OH:23])=[O:22])=[CH:15][CH:14]=2)=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 70 °C

Procedure

Sodium hydroxide (1M, 0.45 ml, 0.45 mmol) was added to a solution of (E)-(S)-ethyl 3-[4-(3-biphenyl-4-yl-but-2-enyloxy)-phenyl]-2-ethoxy-propionate (example 1) (0.100 g, 0.225 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 and the aqueous phase collected. The aqueous phase was acidified with 1N hydrochloric acid (5 ml) and extracted with ethyl acetate (100 ml), and the organic phase collected, 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 a white solid; 0.014 g (15%).

Workup

temperatureAfter cooling to room temperature the resulting mixture
customwas partitioned between water (50 ml) and ethyl acetate
customthe aqueous phase collected
extractionextracted with ethyl acetate (100 ml)
customthe organic phase collected
washwashed with brine
dry with materialdried (Na2SO4)
customevaporated

Sources & evidence

ORD record: ord-9d9ed8d1ddd2476495880091e65c0464
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06867218B2

Reaction notes

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