Water → HCID 89881790, compound
Reaction equation
[C:1]([N:12]1[CH2:17][CH2:16][CH:15]([OH:18])[CH2:14][CH2:13]1)(=[O:11])/[CH:2]=[CH:3]/[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[H-].[Na+].[CH3:21]I.O>C1COCC1>[C:1]([N:12]1[CH2:13][CH2:14][CH:15]([O:18][CH3:21])[CH2:16][CH2:17]1)(=[O:11])/[CH:2]=[CH:3]/[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Compound 8 (0.62 g, 2.4 mmol) was dissolved in THF (10 mL), and sodium hydride (60% in mineral oil) (0.10 g, 2.6 mmol) was added thereto under ice-cooling. After mixing for 15 minutes under ice-cooling, methyl iodide (0.16 mL, 2.6 mmol) was added thereto, and stirred at room temperature for 20 hours. Water was added to the liquid reaction mixture, the mixture was extracted with ethyl acetate, an organic layer was washed with water and saturated sodium chloride solution, and the washed extract was then dried over anhydrous sodium sulfate. The residue was purified with silica gel column chromatography (developing solvent: hexane:ethyl acetate=3:2), to give an intended compound (0.42 g, 65%) in the form of a pale yellow oily substance.
Workup
- temperatureunder ice-cooling
- additionAfter mixing for 15 minutes under ice-
- temperaturecooling
- extractionthe mixture was extracted with ethyl acetate
- washan organic layer was washed with water and saturated sodium chloride solution
- extractionthe washed extract
- dry with materialwas then dried over anhydrous sodium sulfate
- customThe residue was purified with silica gel column chromatography (developing solvent: hexane:ethyl acetate=3:2)
Sources & evidence
- ORD record
- ord-c436f8a347b24992ac57c64db82a81fe
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09428477B2
Reaction notes
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