Methyl iodide → HCID 178495620, compound

HRID 274149Notes

Reaction equation

HRID 274149 reaction equation
[H-].[Na+].[CH3:3]I.[F:5][C:6]([F:22])([F:21])[C:7]1[CH:12]=[CH:11][C:10]([C@H:13]2[CH2:18][CH2:17][C@H:16]([CH2:19][OH:20])[CH2:15][CH2:14]2)=[CH:9][CH:8]=1>C1COCC1>[CH3:3][O:20][CH2:19][C@H:16]1[CH2:15][CH2:14][C@H:13]([C:10]2[CH:9]=[CH:8][C:7]([C:6]([F:21])([F:22])[F:5])=[CH:12][CH:11]=2)[CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178520919HCID 178520919, compound

Product 1

HCID 178495620HCID 178495620, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

60 ml of THF are added under an N2 atmosphere to 100 mmol of NaH in the form of an oil dispersion. The mixture is mixed vigorously and heated to 45°-50° C. 120 mmol of methyl iodide are then added, and 80 mmol of trans-4-(p-trifluoromethylphenyl)cyclohexylmethyl alcohol in 20 ml of THF are subsequently added dropwise over the course of 30 minutes. The reaction mixture is then stirred for 30 minutes at the same temperature, cooled and carefully hydrolysed using aqueous THF. When the vigorous evolution of H2 is complete, customary work-up gives trans-4-methoxymethyl(p-trifluoromethylphenyl)cyclohexane.

Workup

  1. additionThe mixture is mixed vigorously
  2. temperatureheated to 45°-50° C
  3. temperaturecooled

Sources & evidence

ORD record
ord-3c6dfcfdff6340b4a198e2227e916b33
Source dataset
uspto-grants-1995_02
Patent number
US05389295

Reaction notes

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