2-Methylfuran → HCID 89525540, compound

HRID 1050966Notes

Reaction equation

HRID 1050966 reaction equation
C([Li])CCC.[CH3:6][C:7]1[O:8][CH:9]=[CH:10][CH:11]=1.[CH3:12][C:13]1([CH:18]=[O:19])[CH2:17][CH2:16][CH2:15][O:14]1.[Cl-].[NH4+]>CCCCCC.O1CCCC1>[CH3:6][C:7]1[O:8][C:9]([CH:18]([C:13]2([CH3:12])[CH2:17][CH2:16][CH2:15][O:14]2)[OH:19])=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 107972-MethylfuranHCID 25517Ammonium ChlorideHCID 1101883680275-32-7HCID 178418339Butyllithium

Product 1

HCID 89525540HCID 89525540, compoundYield 66.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

24 ml (60 mmol, 1.5 eq) of a 2.5 M solution of n-butyllithium in hexane were added dropwise to a solution of 5.0 g (60 mmol, 1.5 eq) of 2-methylfuran in 100 ml of tetrahydrofuran cooled to −70° C. The reaction medium was stirred and allowed to return to ambient temperature for 2 hours. The reaction medium was cooled to −70° C. and then 6.0 g (40 mmol, 1 eq) of 2-methyltetrahydrofuran-2-carbaldehyde at 77% were added. The reaction medium was stirred at ambient temperature for 3 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, filtered over magnesium sulfate and evaporated. 5.21 g of (5-methylfuran-2-yl)-(2-methyltetrahydrofuran-2-yl)methanol were obtained. Yield=66%. TLC/SiO2: heptane/EtOAc (60/40), developing with KMnO4.

Workup

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

Sources & evidence

ORD record
ord-ea658317c56342378f14233e25367ecf
Source dataset
uspto-grants-2016_07
Patent number
US09388149B2

Reaction notes

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