Sodium Hydroxide → (E)-(S)-3-{4-[3-(4-bromophenyl)-but-2-enyloxy]-phenyl}-2-ethoxy-propionic acid
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]=1Participants
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
- customThe resulting mixture was partitioned between water (50 ml) and ethyl acetate (50 ml)
- additionthe aqueous layer acidified to pH1 by addition of 1N HCl
- customThe aqueous layer was separated
- extractionfurther extracted with ethyl acetate (2×50 ml)
- washThe combined organic layers were washed with brine
- dry with materialdried (MgSO4)
- customevaporated
- customvacuum dried at 40° C. for 18 h
Sources & evidence
- ORD record
- ord-4fc4937047034ac49fa5dfe7f85c91e8
- Source dataset
- uspto-grants-2003_04
- Patent number
- US06555577B1
Reaction notes
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