Methanol → HCID 18759786, compound

HRID 275749Notes

Reaction equation

HRID 275749 reaction equation
C([N-]C(C)C)(C)C.[Li+].[CH3:9][N:10]1[CH2:14][CH2:13][CH2:12][C:11]1=[O:15].[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23]Cl)=[CH:19][N:18]=1.CO>C1CCCCC1.O1CCCC1>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH:12]2[CH2:13][CH2:14][N:10]([CH3:9])[C:11]2=[O:15])=[CH:19][N:18]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 13387N-methyl-2-pyrrolidoneHCID 1554792-Chloro-5-(chloromethyl)pyridineHCID 2724682Lithium diisopropylamide

Product 1

HCID 18759786HCID 18759786, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8078CyclohexaneSolvent

Procedure

Under an argon atmosphere at a temperature of from −78° C. to −60° C., 150 ml of a 1.5 molar solution of lithium diisopropylamide (LDA) in cyclohexane are added dropwise in the course of one hour to 20 g of N-methylpyrrolid-2-one in 50 ml of tetrahydrofuran (THF) and the reaction mixture is stirred at the same temperature for a further one hour. Then, at from −78° C. to −60° C., 25.0 g of 2-chloro-5-(chloromethyl)-pyridine in 40 ml of THF are added, and the mixture is stirred for a further 6 hours at that temperature and then for a further 6 hours at 0° C. 15 ml of methanol are added and the reaction mixture is then poured onto a mixture of ice/water and extracted with ethyl acetate, and the organic phase is separated off. The ethyl acetate phase is dried over magnesium sulfate and concentrated to dryness by evaporation in vacuo. The residue is purified on silica gel using ethyl acetate/hexane (7:1) as eluant The title compound (compound 1.4) is obtained in the form of a colourless oil.

Workup

  1. stirringthe mixture is stirred for a further 6 hours at that temperature
  2. waitfor a further 6 hours at 0° C
  3. extractionextracted with ethyl acetate
  4. customthe organic phase is separated off
  5. dry with materialThe ethyl acetate phase is dried over magnesium sulfate
  6. concentrationconcentrated to dryness by evaporation in vacuo
  7. customThe residue is purified on silica gel
  8. customis obtained in the form of a colourless oil

Sources & evidence

ORD record
ord-aa5e57d5df4b4ebfb13f0701f3b4ce77
Source dataset
uspto-grants-2002_03
Patent number
US06353001B1

Reaction notes

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