Diethyl Ether → HCID 14810227, compound

HRID 2377121Notes

Reaction equation

HRID 2377121 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([O:8]C)=O.[CH2:10]([Mg]Br)[CH3:11].C(=O)(O)[O-].[Na+].[CH2:19](OCC)[CH3:20]>C1COCC1.O>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([OH:8])([CH2:10][CH3:11])[CH2:19][CH3:20]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 11902Methyl 2-furoateHCID 516892Sodium BicarbonateHCID 178418443HCID 178418443, compound

Product 1

HCID 14810227HCID 14810227, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-30 °C

Procedure

2-methyl furate (10.0 g, 79 mmol) is dissolved in THF (100 mL) under a nitrogen atmosphere. Ethyl magnesium bromide (3.0 M in Et2O, 55 ml, 166 mmol) is added initially at room temperature. The reaction is cooled to −30° C., and the remaining ethyl Grignard added. The mixture is stirred overnight at room temperature. Saturated sodium bicarbonate solution (10 mL) is added to the stirring solution followed by diethyl ether (100 mL) and water (50 mL). The organic layer is separated and washed with water. The ether layer is dried over magnesium sulfate, filtered, and evaporated under vacuum to give 10.7 g of a oil, which was used without further purification.

Workup

  1. customThe organic layer is separated
  2. washwashed with water
  3. dry with materialThe ether layer is dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-20e1c7800b4f4e138dbce1924d3a1bb0
Source dataset
uspto-grants-2008_12
Patent number
US07468449B2

Reaction notes

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