2-Methylfuran → HCID 89525590, compound

HRID 1528147Notes

Reaction equation

HRID 1528147 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:17]=[O:18])[CH2:16][O:15][CH2:14]1.[Cl-].[NH4+]>CCCCCC.O1CCCC1>[CH3:6][C:7]1[O:8][C:9]([CH:17]([C:13]2([CH3:12])[CH2:16][O:15][CH2:14]2)[OH:18])=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 107972-MethylfuranHCID 25517Ammonium ChlorideHCID 189624683-Methyloxetane-3-carbaldehydeHCID 178418339Butyllithium

Product 1

HCID 89525590HCID 89525590, compoundYield 92.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

12.0 ml (30 mmol, 1.7 eq) of a 2.5 M solution of n-butyllithium in hexane were added dropwise to a solution of 2.46 g (30 mmol, 1.7 eq) of 2-methylfuran in 50 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 2.17 g (18 mmol, 1 eq) of 3-methyloxetane-3-carbaldehyde at 83% 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 and evaporated. 3.02 g of (5-methylfuran-2-yl)-(3-methyloxetan-3-yl)methanol were obtained in the form of an orange oil. Yield=92%.

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. customevaporated

Sources & evidence

ORD record
ord-359fd5d9fc28466ba44431a5ebce409d
Source dataset
uspto-grants-2015_07
Patent number
US09090596B2

Reaction notes

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