Tetrahydrofuran → HCID 10511974, compound

HRID 376288Notes

Reaction equation

HRID 376288 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1(C#N)[CH:11]=[CH:10][CH:9]=[CH:8][NH:7]1.C[Mg]Br.[Cl-].[NH4+].[O:19]1CC[CH2:21][CH2:20]1>C(OCC)C>[O:3]1[CH2:4][CH2:5][O:1][CH:2]1[C:6]1[N:7]=[C:8]([C:20](=[O:19])[CH3:21])[CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 19361763HCID 19361763, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 10511974HCID 10511974, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-10 °C

Procedure

0.88 g of 2-[1,3]dioxolan-2-yl-pyridine-2-carbonitrile (4.99 mmol) is dissolved in 10 ml of tetrahydrofuran. 3.50 ml of a 3M solution of methylmagnesium bromide in diethyl ether are introduced dropwise into the solution cooled to -10° C. The reaction mixture is stirred for 3 hours at room temperature under a nitrogen atmosphere. The mixture is poured into a saturated aqueous solution of ammonium chloride, the mixture is extracted with ethyl acetate, the organic phase is washed with a saturated aqueous solution of ammonium chloride and then dried over magnesium sulfate, filtered and concentrated under vacuum. The title product is isolated by chromatography on a silica column (eluent: chloroform). 0.80 g of a yellow oil is recovered.

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. washthe organic phase is washed with a saturated aqueous solution of ammonium chloride
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-71195cf600bb4e749bcd42f540b712b8
Source dataset
uspto-grants-2000_02
Patent number
US06020345

Reaction notes

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