Ethyl Acetate → HCID 55139138, compound

HRID 2400556Notes

Reaction equation

HRID 2400556 reaction equation
[H-].[Na+].[O:3]1[CH2:8][CH2:7][CH:6]([OH:9])[CH2:5][CH2:4]1.Br[CH2:11][C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=1.C(OCC)(=O)C>C1COCC1>[O:3]1[CH2:8][CH2:7][CH:6]([O:9][CH2:11][C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=2)[CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 74956Tetrahydro-4H-pyran-4-olHCID 869964-(Bromomethyl)benzonitrile

Product 1

HCID 55139138HCID 55139138, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of sodium hydride (60% dispersion in mineral oil; 490 mg, 12.2 mmol) in THF (10 mL) was added a solution of tetrahydro-2H-pyran-4-ol (1.20 g, 12.2 mmol) in THF (2 mL) at rt. The reaction mixture was stirred at it for several minutes and then heated to reflux for 15 min. After cooling to rt, 4-(bromomethyl)benzonitrile (2.00 g, 10.2 mmol) was added, and the reaction mixture was stirred at it over night. Ethyl acetate was added and the mixture was washed with water. The organic layer was dried with anhydrous magnesium sulfate and filtered. After evaporation of the solvent, the crude product was purified by MPLC (silica, cyclohexane/ethyl acetate 7:3) to afford the title compound (1.57 g, 71%): 1H NMR (400 MHz, CDCl3) δ 7.53 (d, 2H), 7.45 (d, 2H), 4.61 (s, 2H), 4.00-3.92 (m, 2H), 3.65-3.58 (m, 1H), 3.49-3.41 (m, 2H), 1.99-1.92 (m, 2H), 1.72-1.62 (m, 2H); ES-MS m/z 218, HPLC RT (Method D) 1.86 min.

Workup

  1. temperatureheated
  2. temperatureto reflux for 15 min
  3. stirringthe reaction mixture was stirred at it over night
  4. washthe mixture was washed with water
  5. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customAfter evaporation of the solvent
  8. customthe crude product was purified by MPLC (silica, cyclohexane/ethyl acetate 7:3)

Sources & evidence

ORD record
ord-5aa8e7ff6a0f42d28cb358b84d61e755
Source dataset
uspto-grants-2014_08
Patent number
US08796253B2

Reaction notes

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