Methyl iodide → HCID 178496627, compound

HRID 406049Notes

Reaction equation

HRID 406049 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[C:6]([O:13][C@H:14]2[CH2:19][CH2:18][C@H:17]([OH:20])[CH2:16][CH2:15]2)[CH:5]=1.I[CH3:22]>CN(C=O)C.CCOC(C)=O>[F:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[C:6]([O:13][C@H:14]2[CH2:15][CH2:16][C@H:17]([O:20][CH3:22])[CH2:18][CH2:19]2)[CH:5]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178526647HCID 178526647, compound

Product 1

HCID 178496627HCID 178496627, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.6 g sodium hydride (60%) were added to a cooled solution (−7° C.) of 2.55 g 4-fluoro-2-(trans-4-hydroxy-cyclohexyloxy)-1-nitro-benzene and iodomethane in 30 ml DMF. The mixture was allowed to warm to rt overnight, diluted with EtOAc and washed with water and brine (3×). The organic phase was dried (MgSO4), passed through a hydrophobic frit and evaporated. The residue was purified by flash column chromatography (silica gel, 100% i-hexane→7:1 i-hexane:EtOAc).

Workup

  1. washwashed with water and brine (3×)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. customevaporated
  4. customThe residue was purified by flash column chromatography (silica gel, 100% i-hexane→7:1 i-hexane:EtOAc)

Sources & evidence

ORD record
ord-7ede57af252d410699b6107680f06c7a
Source dataset
uspto-grants-2014_06
Patent number
US08754079B2

Reaction notes

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