2-Methylfuran → HCID 89525470, compound

HRID 1528152Notes

Reaction equation

HRID 1528152 reaction equation
C([Li])CCC.[CH3:6][C:7]1[O:8][CH:9]=[CH:10][CH:11]=1.[F:12][CH2:13][C:14]1([CH:18]=[O:19])[CH2:17][O:16][CH2:15]1.[Cl-].[NH4+]>CCCCCC.O1CCCC1>[F:12][CH2:13][C:14]1([CH:18]([C:9]2[O:8][C:7]([CH3:6])=[CH:11][CH:10]=2)[OH:19])[CH2:17][O:16][CH2:15]1

Participants

7

Reactant 4

HCID 107972-MethylfuranHCID 25517Ammonium ChlorideHCID 89525390HCID 89525390, compoundHCID 178418339Butyllithium

Product 1

HCID 89525470HCID 89525470, compoundYield 106.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

11.0 ml (27 mmol, 1.5 eq) of a 2.5 M solution of n-butyllithium in hexane were added dropwise to a solution of 2.25 g (27 mmol, 1.5 eq) of 2-methylfuran in 40 ml of tetrahydrofuran cooled to −70° C. The reaction medium was stirred and allowed to return to ambient temperature for 3 hours. The reaction medium was cooled to −70° C. and then 2.16 g (18 mmol, 1 eq) of 3-fluoromethyloxetane-3-carbaldehyde were added. The reaction medium was stirred at ambient temperature for two and a half hours. The reaction medium was treated with a saturated ammonium chloride solution and extracted with ethyl acetate. The organic phases were combined, washed with a saturated sodium chloride solution and evaporated. 3.83 g of (3-fluoromethyloxetan-3-yl)-(5-methylfuran-2-yl)methanol were obtained in the form of a dark orange oil. Yield=71%. TLC SiO2/CH2Cl2:MeOH (96/4), developing with KMnO4.

Workup

  1. temperatureThe reaction medium was cooled to −70° C.
  2. stirringThe reaction medium was stirred at ambient temperature for two and a half hours
  3. extractionextracted with ethyl acetate
  4. washwashed with a saturated sodium chloride solution
  5. customevaporated

Sources & evidence

ORD record
ord-956c1ce8945e4c18a87dfd598a3a12ab
Source dataset
uspto-grants-2015_07
Patent number
US09090596B2

Reaction notes

Loading…