Iodoethane → Methyl 2-((ethyloxy)methyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate

HRID 1662480Notes

Reaction equation

HRID 1662480 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][C:11]=1[CH2:20][OH:21].[H-].[Na+].[CH2:24](I)[CH3:25]>CN(C=O)C.CCOC(C)=O>[CH2:24]([O:21][CH2:20][C:11]1[CH:12]=[C:13]([C:16]([O:18][CH3:19])=[O:17])[CH:14]=[CH:15][C:10]=1[C:3]1[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=1[F:1])[CH3:25]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 57707070Methyl 2'-fluoro-2-(hydroxymethyl)-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate

Product 1

HCID 57705798Methyl 2-((ethyloxy)methyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-carboxylateYield 79%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 66.63A (0.200 g, 0.689 mmol) in DMF (5 mL), was added NaH (0.0198 g, 0.827 mmol). The reaction was stirred at room temperature for 10 minutes. Ethyl iodide was then added and the reaction was stirred at room temperatures for 1 hour. The mixture was diluted with EtOAc, washed with water and brine, and dried over anhydrous Na2SO4. After removing solvent, the residue was purified by flash chromatography (silica gel, 1:1 EtOAc/hexane) and gave 67.23A in 79% yield. MS ESI (pos.) m/e: 336 (M+18)+.

Workup

  1. stirringthe reaction was stirred at room temperatures for 1 hour
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. customAfter removing solvent
  5. customthe residue was purified by flash chromatography (silica gel, 1:1 EtOAc/hexane)

Sources & evidence

ORD record
ord-05c4e8d57df14a599cf7460bc7def1a8
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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