Methanol → HCID 10824589, compound
Reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4](S(O)(=O)=O)=[CH:3][CH:2]=1.C([O:15][CH:16]([CH3:18])[CH3:17])(C)C.[OH2:19].[CH3:20][OH:21]>>[CH3:2][CH:1]([CH3:11])[CH2:6][CH2:18][CH:16]([OH:15])[CH2:17][C:20]([O:21][CH2:11][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:19]Participants
Procedure
To a solution of the benzyl ester (3.11 g) obtained in Synthesis Example 80 in methanol (70 ml) was added p-toluenesulfonic acid (0.35 g) and the mixture was heated under reflux for one hour. After cooling to room temperature, isopropyl ether and water were added thereto. The organic layer was separated and the aqueous layer was extracted with isopropyl ether. The extract was combined with the organic layer and washed with water, a saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate. After the solvent was removed in vacuo under reduced pressure, the residue was purified by a silica gel column chromatography (silica gel 70 g, hexane: ethyl acetate=100:15) to afford 1.38 g of benzyl 6-methyl-3-hydroxyheptanoate.
Workup
- temperaturethe mixture was heated
- temperatureunder reflux for one hour
- customThe organic layer was separated
- extractionthe aqueous layer was extracted with isopropyl ether
- washwashed with water
- dry with materiala saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate
- customAfter the solvent was removed in vacuo under reduced pressure
- customthe residue was purified by a silica gel column chromatography (silica gel 70 g, hexane: ethyl acetate=100:15)
Sources & evidence
- ORD record
- ord-e1c90daa1155484ba6cc1f2c570561b8
- Source dataset
- uspto-grants-2005_02
- Patent number
- US06858585B1
Reaction notes
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