Potassium Hydroxide → (S)-6-(benzyloxy)-2-((R)-2-(4-fluorophenyl)-2-hydroxyethyl)hex-4-enoic acid
Reaction equation
[CH2:1]([O:8][CH2:9][CH:10]=[CH:11][CH2:12][C@H:13]1[CH2:17][C@H:16]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[O:15][C:14]1=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:26].[K+]>O1CCOCC1>[CH2:1]([O:8][CH2:9][CH:10]=[CH:11][CH2:12][C@@H:13]([CH2:17][C@H:16]([C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)[OH:15])[C:14]([OH:25])=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
4
Procedure
To a solution of (3S,5R)-3-(4-(benzyloxy)but-2-enyl)-5-(4-fluorophenyl)dihydrofuran-2(3H)-one (643 mg, 1.9 mmol) in 7 mL dioxane was added 7 mL aqueous 5% KOH at 25° C. After being stirred for 30 min at room temperature the reaction was quenched by the addition of 10 mL of 1M aqueous HCl. The mixture was extracted ethyl acetate (2×50 mL) and the combined organic layers were washed with brine (2×30 mL). The solution was dried over Na2SO4 before being concentrated under reduced pressure. The crude product was used directly in the next reaction without further purification.
Workup
- customwas quenched by the addition of 10 mL of 1M aqueous HCl
- extractionThe mixture was extracted ethyl acetate (2×50 mL)
- washthe combined organic layers were washed with brine (2×30 mL)
- dry with materialThe solution was dried over Na2SO4
- concentrationbefore being concentrated under reduced pressure
- customThe crude product was used directly in the next reaction without further purification
Sources & evidence
- ORD record
- ord-dabf7dd7bdcb46c48cfa2e0fbb2ed237
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08119692B2
Reaction notes
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