Thionyl Chloride → 2-{4-[Chloro(cyclohexyl)methyl]-5-methylfuran-2-yl}-5-fluoropyridine

HRID 1877085Notes

Reaction equation

HRID 1877085 reaction equation
[CH:1]1([CH:7]([C:9]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][N:15]=3)[O:11][C:10]=2[CH3:21])O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)([Cl:24])=O>C1(C)C=CC=CC=1>[Cl:24][CH:7]([CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[C:9]1[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][N:15]=2)[O:11][C:10]=1[CH3:21]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 68515149Cyclohexyl[5-(5-fluoropyridin-2-yl)-2-methylfuran-3-yl]methanol

Product 1

HCID 685096942-{4-[Chloro(cyclohexyl)methyl]-5-methylfuran-2-yl}-5-fluoropyridineYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of cyclohexyl[5-(5-fluoropyridin-2-yl)-2-methylfuran-3-yl]methanol (0.7 g) in toluene (10 mL) was added thionyl chloride (0.3 mL), and the mixture was stirred at room temperature for 2 hr. The solvent was evaporated under reduced pressure to give the title compound (0.7 g, 100%) as a yellow crystal.

Workup

  1. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-5b8c7b5ecba34c71b5409145225bb62c
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Reaction notes

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