2-Methylfuran → (5-Methylfuran-2-yl)-(tetrahydropyran-4-yl)methanol

HRID 2271503Notes

Reaction equation

HRID 2271503 reaction equation
C([Li])CCC.[CH3:6][C:7]1[O:8][CH:9]=[CH:10][CH:11]=1.[O:12]1[CH2:17][CH2:16][CH:15]([CH:18]=[O:19])[CH2:14][CH2:13]1.[Cl-].[NH4+]>CCCCCC.O1CCCC1>[CH3:6][C:7]1[O:8][C:9]([CH:18]([CH:15]2[CH2:16][CH2:17][O:12][CH2:13][CH2:14]2)[OH:19])=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 107972-MethylfuranHCID 25517Ammonium ChlorideHCID 9964078Tetrahydro-2H-pyran-4-carboxaldehydeHCID 178418339Butyllithium

Product 1

HCID 63937679(5-Methylfuran-2-yl)-(tetrahydropyran-4-yl)methanolYield 112.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

12.0 ml (30 mmol, 1.5 eq) of a 2.5 M solution of n-butyllithium in hexane were added dropwise to a solution of 2.46 g (30 mmol, 1.5 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 2 hours. The reaction medium was cooled to −70° C. and then 2.28 g (20 mmol, 1 eq) of tetrahydro-2H-pyran-4-carbaldehyde were added. The reaction medium was stirred at ambient temperature for 2 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. 4.43 g of (5-methylfuran-2-yl)-(tetrahydropyran-4-yl)methanol were obtained. Yield=100%.

Workup

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

Sources & evidence

ORD record
ord-50841de309854a4a9f9697b51b1fc2dc
Source dataset
uspto-grants-2015_09
Patent number
US09120772B2

Reaction notes

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