Tetrahydrofuran → HCID 23284516, compound

HRID 368976Notes

Reaction equation

HRID 368976 reaction equation
O1CCCC1.[Cl:6][C:7]1[N:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=O.[CH:17]1([Mg]Cl)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.[Cl-].[NH4+]>CCOCC>[Cl:6][C:7]1[C:8]([C:9]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[O:11])=[CH:12][CH:13]=[C:14]([CH3:16])[N:15]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 1217242-Chloro-6-methylnicotinic acidHCID 178478990HCID 178478990, compound

Product 1

HCID 23284516HCID 23284516, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A tetrahydrofuran (30 ml) solution of 2-chloro-6-methylnicotinic acid (3.43 g, 20 mmol) was cooled to -40° C., mixed with ether (30 ml) solution of 2.0 M cyclohexyl magnesium chloride and stirred overnight at room temperature. The reaction solution was poured into saturated ammonium chloride aqueous solution and extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. After removing magnesium sulfate by filtration, the filtrate was concentrated under a reduced pressure and the resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give 2-chloro-3-cyclohexylcarbonyl-6-methylpyridine (650 mg, 14%) as a brown oily material.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customAfter removing magnesium sulfate
  5. filtrationby filtration
  6. concentrationthe filtrate was concentrated under a reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-dde90c01eb744b2088c912fdca3470ed
Source dataset
uspto-grants-2000_10
Patent number
US06136810

Reaction notes

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