Methyl iodide → HCID 178495004, compound

HRID 249223Notes

Reaction equation

HRID 249223 reaction equation
[H-].[Na+].[CH3:3]I.[CH3:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C@H:13]2[CH2:18][CH2:17][C@H:16]([CH2:19][CH2:20][CH2:21][OH:22])[CH2:15][CH2:14]2)=[CH:9][CH:8]=1>C1COCC1>[CH2:19]([C@H:16]1[CH2:17][CH2:18][C@H:13]([C:10]2[CH:11]=[CH:12][C:7]([O:6][CH3:5])=[CH:8][CH:9]=2)[CH2:14][CH2:15]1)[CH2:20][CH2:21][O:22][CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178490594HCID 178490594, compound

Product 1

HCID 178495004HCID 178495004, 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 stirred vigorously and heated to 45° C.-50° C. 120 mmol of methyl iodide are then added, and 80 mmol of trans-4-(p-methoxyphenyl)cyclohexylpropyl alcohol [prepared as described above by malonic ester synthesis and reduction using LiAlH4 ] in 20 ml of THF are subsequently added dropwise over the course of 30 minutes. The mixture is subsequently stirred for a further 30 minutes at the same temperature, and the reaction mixture is then cooled and carefully hydrolyzed using aqueous THF. When the vigorous evolution of H2 is complete, the mixture is subjected to customary work-up, giving trans-4-(4-oxapentyl)-(p-methoxyphenyl)cyclohexane, C 19 N (15.1) I.

Workup

  1. temperatureheated to 45° C.-50° C
  2. stirringThe mixture is subsequently stirred for a further 30 minutes at the same temperature
  3. temperaturethe reaction mixture is then cooled

Sources & evidence

ORD record
ord-5936e7bc549e4b6fb065ba034a5c7d12
Source dataset
uspto-grants-1993_05
Patent number
US05213710

Reaction notes

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