Diethyl Ether → 3-butylfuran
Reaction equation
C([Li])(C)(C)C.[CH3:6][CH2:7][CH2:8][CH2:9]C.[CH3:11][CH2:12][O:13][CH2:14][CH3:15]>>[CH2:6]([C:11]1[CH:15]=[CH:14][O:13][CH:12]=1)[CH2:7][CH2:8][CH3:9]Participants
4
Conditions
- Temperature
- -78 °C
Procedure
The iodo-product obtained from Step B above (2.2 g, 8.8 mmol) was dissolved in 60 mL of ether, and stirred in a −78° C. bath. A 1.7 M solution of t-butyllithium in pentane (10.4 mL, 17.7 mmol) was added dropwise. After 20 min, cooling bath was removed. Reaction was continued for 2.5 hr and quenched with H2O (20 mL). The aqueous mixture was stirred overnight and separated. The aqueous layer was extracted with ether (30 mL). The combined organic layers were washed with brine, dried by Na2SO4, and filtered through a Celite pad. Removal of solvent gave 1.10 g (100%) of 3-butylfuran as a reddish-yellow oil.
Workup
- temperaturecooling bath
- customwas removed
- customReaction
- waitwas continued for 2.5 hr
- customquenched with H2O (20 mL)
- stirringThe aqueous mixture was stirred overnight
- customseparated
- extractionThe aqueous layer was extracted with ether (30 mL)
- washThe combined organic layers were washed with brine
- dry with materialdried by Na2SO4
- filtrationfiltered through a Celite pad
- customRemoval of solvent
Sources & evidence
- ORD record
- ord-4c448dcadcf34e2dbd61f571b30ef65b
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07786149B2
Reaction notes
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