Cyclohexanol → HCID 86681315, compound

HRID 1430270Notes

Reaction equation

HRID 1430270 reaction equation
[CH:1]1([OH:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].F[C:11]1[C:16]([CH3:17])=[C:15]([I:18])[CH:14]=[CH:13][N:12]=1>O1CCCC1>[CH:1]1([O:7][C:11]2[C:16]([CH3:17])=[C:15]([I:18])[CH:14]=[CH:13][N:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 7966CyclohexanolHCID 24758Sodium hydrideHCID 117762982-Fluoro-4-iodo-3-methylpyridine

Product 1

HCID 86681315HCID 86681315, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Cyclohexanol (0.501 g) in tetrahydrofuran (3.5 mL) was treated with NaH (0.1 g) until gas evolution ceased. 2-Fluoro-4-iodo-3-methylpyridine (0.237 g) in tetrahydrofuran (1.5 mL) was added. The reaction mixture was stirred at room temperature for 0.5 hours and was quenched with ice-water. The resulting mixture was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated. The residue was purified by preparative TLC, and was eluted with petroleum ether to provide the title compound.

Workup

  1. customwas quenched with ice-water
  2. extractionThe resulting mixture was extracted with ethyl acetate
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by preparative TLC
  8. washwas eluted with petroleum ether

Sources & evidence

ORD record
ord-d5e56a29f56245b7a0f4b6e3af6181af
Source dataset
uspto-grants-2015_01
Patent number
US08940737B2

Reaction notes

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