Ethylene Oxide → HCID 63967771, compound
Reaction equation
[CH2:1]([C:3]1[S:4][CH:5]=[CH:6][CH:7]=1)[CH3:2].[Li]CCCC.[CH2:13]1[O:15][CH2:14]1>C(OCC)C>[CH2:1]([C:3]1[S:4][C:5]([CH2:14][CH2:13][OH:15])=[CH:6][CH:7]=1)[CH3:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2-ethylthiophene (2 g, 17.85 mmol, 1 eq) in anhydrous diethyl ether at 0° C. was added n-BuLi (8.6 mL, 21.4 mmol, 2.5 M in hexanes, 1.2 eq) over 15 minutes. The mixture was stirred at room temperature for 30 minutes. After cooling to 0° C., a solution of ethylene oxide (1.1 mL, 21.4 mmol, 1.2 eq) in anhydrous ether was added. After stirring at 0° C. for 3 hr, the reaction mixture was quenched with water and extracted with diethyl ether. The organic layer was dried over Na2SO4 and concentrated to give a crude product. The crude product was purified by column chromatography.
Workup
- temperatureAfter cooling to 0° C.
- stirringAfter stirring at 0° C. for 3 hr
- customthe reaction mixture was quenched with water
- extractionextracted with diethyl ether
- dry with materialThe organic layer was dried over Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-1352dc5b9aa148388e942fce61f6bb9f
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08710245B2
Reaction notes
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