Tetrahydrofuran → HCID 59517152, compound

HRID 1161425Notes

Reaction equation

HRID 1161425 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].C(N1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)=O.[Cl-].[NH4+].[C:16]([O:19][CH2:20]C)(=[O:18])C.C1C[O:25][CH2:24]C1>>[CH2:12]([O:11][C:10]1[C:9]2[O:18][CH2:16][O:19][CH2:20][C:1]=2[CH:2]=[C:3]([CH:24]=[O:25])[CH:4]=1)[CH3:13]

Participants

6

Reactant 5

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 20417N-FormylmorpholineHCID 25517Ammonium ChlorideHCID 178418339Butyllithium

Product 1

HCID 59517152HCID 59517152, compound

Conditions

Temperature
-70 °C

Procedure

To a solution of 1.62 g of this compound in 30 ml of THF there was added dropwise 2.8 ml of n-butyllithium (2.62 M, hexane solution) at −70° C. under a nitrogen atmosphere. After stirring at −70° C. for 30 minutes, 1 ml of N-formylmorpholine was added and the temperature was raised from −70° C. to 0° C. over a period of 30 minutes. Saturated aqueous ammonium chloride was added to the reaction mixture, and extraction was performed with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane) to give the title compound (773 mg).

Workup

  1. temperaturethe temperature was raised from −70° C. to 0° C. over a period of 30 minutes
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationThe desiccating agent was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane)

Sources & evidence

ORD record
ord-dd27ffaf1ab24d00a3a8e0d06cc785fe
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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