Methyl iodide → HCID 20042584, compound

HRID 1762165Notes

Reaction equation

HRID 1762165 reaction equation
[F:1][C:2]([F:31])([F:30])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:19]2[CH:24]=[CH:23][C:22]([O:25][C:26]([F:29])([F:28])[F:27])=[CH:21][CH:20]=2)([OH:18])[CH:11]([N:13]2[N:17]=[N:16][CH:15]=[N:14]2)[CH3:12])=[CH:6][CH:5]=1.[H-].[Na+].[CH3:34]I>CN(C)C=O.O>[F:29][C:26]([F:27])([F:28])[O:25][C:22]1[CH:23]=[CH:24][C:19]([C:10]([C:7]2[CH:8]=[CH:9][C:4]([O:3][C:2]([F:1])([F:30])[F:31])=[CH:5][CH:6]=2)([O:18][CH3:34])[CH:11]([N:13]2[N:17]=[N:16][CH:15]=[N:14]2)[CH3:12])=[CH:20][CH:21]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 20042590HCID 20042590, compound

Product 1

HCID 20042584HCID 20042584, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1,1-bis(4-trifluoromethoxyphenyl)-2-(2H-tetrazol-2-yl)propanol (220 g) was added to a stirred suspension of sodium hydride (24 mg of a 50% dispension in oil) in dry dimethylformamide (6.0 cm3) at the ambient temperature under a nitrogen atmosphere, and the mixture stirred for a further 2 hours after which methyl iodide (71 mg) was added and the resultant mixtures stirred for a further 20 hours. After diluting with water the mixture was extracted with diethyl ether (3×15 cm3), the extracts were combined, dried over anhydrous magnesium sulphate and concentrated by evaporation of the solvent under reduced pressure. The residual yellow oil was subjected to h.p.l.c using a silica gel column eluted with a mixture of n-hexane and ethyl acetate (5:1 by volume) to yield 1,1-bis(4-trifluoromethoxyphenyl)-1-methoxy-2-(2H-tetrazol-2-yl)propane.

Workup

  1. additionwas added
  2. extractionwas extracted with diethyl ether (3×15 cm3)
  3. dry with materialdried over anhydrous magnesium sulphate
  4. concentrationconcentrated by evaporation of the solvent under reduced pressure
  5. washeluted with a mixture of n-hexane and ethyl acetate (5:1 by volume)

Sources & evidence

ORD record
ord-2b7fd86256234446a363e65c96a8f7c4
Source dataset
uspto-grants-1989_05
Patent number
US04831047

Reaction notes

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