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

HRID 984330Notes

Reaction equation

HRID 984330 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12](/[C:15](/[CH3:35])=[CH:16]/[CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:25][C@H:26]([O:32][CH2:33][CH3:34])[C:27]([O:29]CC)=[O:28])=[CH:21][CH:20]=2)=[CH:11][CH:10]=1.[OH-].[Na+]>>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[CH:11][C:12](/[C:15](/[CH3:35])=[CH:16]/[CH2:17][O:18][C:19]2[CH:20]=[CH:21][C:22]([CH2:25][C@H:26]([O:32][CH2:33][CH3:34])[C:27]([OH:29])=[O:28])=[CH:23][CH:24]=2)=[CH:13][CH:14]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 86589950(E)-(S)-ethyl 3-{4-[3-(2',3'-dichloro-biphenyl-4-yl)-but-2-enyloxy]-phenyl}-2-ethoxy-propionate

Product 1

HCID 69797134(E)-(S)-3-{4-[3-(2',3'-dichloro-biphenyl-4-yl)-but-2-enyloxy]-phenyl}-2-ethoxy-propionic acid

Procedure

The title compound was prepared from (E)-(S)-ethyl 3-{4-[3-(2′,3′-dichloro-biphenyl-4-yl)-but-2-enyloxy]-phenyl}-2-ethoxy-propionate (example 58) (0.325 g, 0.63 mmol) and sodium hydroxide (1M, 1.27 ml, 1.27 mmol) by a procedure analogous to that described in example 51, giving (E)-(S)-3-{4-[3-(2′,3′-dichloro-biphenyl-4-yl)-but-2-enyloxy]-phenyl}-2-ethoxy-propionic acid as a gum, which contained 0.28 mol equivalents of ethyl acetate; 0.24 g (80%).

Sources & evidence

ORD record
ord-49f0764b15d1452abc8948d3215ddd60
Source dataset
uspto-grants-2005_03
Patent number
US06867218B2

Reaction notes

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