HCID 85700288, compound → HCID 14924162, compound
Reaction equation
[OH:1][CH:2]([CH2:10][CH2:11][CH:12]=[CH2:13])[CH:3]([CH3:9])[C:4]([O:6]CC)=[O:5]>[OH-].[K+].CO>[OH:1][CH:2]([CH2:10][CH2:11][CH:12]=[CH2:13])[CH:3]([CH3:9])[C:4]([OH:6])=[O:5]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
Ethyl 3-hydroxy-2-methylhept-6-enoate (6.11 g, 32.8 mmol) was dissolved in a 2 N potassium hydroxide-methanol solution (100 mL), and the mixture was stirred at room temperature for 2 hours and then left overnight. The methanol was distilled off under reduced pressure, and the residue was diluted with water, then washed with methylene chloride, and then neutralized with dilute hydrochloric acid. The aqueous layer was subjected to extraction with ethyl acetate, and the extract was washed with water and saturated saline and dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure to obtain the compound of interest as a pale yellow oil (5.46 g).
Workup
- waitleft overnight
- distillationThe methanol was distilled off under reduced pressure
- additionthe residue was diluted with water
- washwashed with methylene chloride
- extractionThe aqueous layer was subjected to extraction with ethyl acetate
- washthe extract was washed with water and saturated saline
- dry with materialdried over anhydrous magnesium sulfate
- distillationThen, the solvent was distilled off under reduced pressure
Sources & evidence
- ORD record
- ord-b35468e5cfb34401a74d074484572180
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07947738B2
Reaction notes
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