Diethyl Ether → 3-butylfuran

HRID 551293Notes

Reaction equation

HRID 551293 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

Reactant 3

HCID 3283Diethyl EtherHCID 8003PentaneHCID 178418306HCID 178418306, compound

Product 1

HCID 122242583-butylfuranYield 100%

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 h, 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

  1. temperaturecooling bath
  2. customwas removed
  3. customReaction
  4. waitwas continued for 2.5 h
  5. customquenched with H2O (20 mL)
  6. stirringThe aqueous mixture was stirred overnight
  7. customseparated
  8. extractionThe aqueous layer was extracted with ether (30 mL)
  9. washThe combined organic layers were washed with brine
  10. dry with materialdried by Na2SO4
  11. filtrationfiltered through a Celite pad
  12. customRemoval of solvent

Sources & evidence

ORD record
ord-6f73edc5f1284dae831f77267cde5a77
Source dataset
uspto-grants-2011_05
Patent number
US07947720B2

Reaction notes

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