Methyl iodide → HCID 178495002, compound

HRID 1975613Notes

Reaction equation

HRID 1975613 reaction equation
[H-].[Na+].O1CCC[CH2:4]1.[Br:8][C:9]1[CH:14]=[CH:13][C:12]([C@H:15]2[CH2:20][CH2:19][C@H:18](/[CH:21]=[CH:22]/[CH2:23][OH:24])[CH2:17][CH2:16]2)=[CH:11][CH:10]=1.CI>O>[Br:8][C:9]1[CH:10]=[CH:11][C:12]([C@H:15]2[CH2:16][CH2:17][C@H:18](/[CH:21]=[CH:22]/[CH2:23][O:24][CH3:4])[CH2:19][CH2:20]2)=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 178520635HCID 178520635, compound

Product 1

HCID 178495002HCID 178495002, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.5 g of sodium hydride and 50 ml of tetrahydrofuran was treated with 2.6 g of 1-bromo-4-[trans-4-[(E)-3-hydroxypropenyl]cyclohexyl]benzene while gassing with nitrogen, stirred for 2 hours, treated with 1.6 g of methyl iodide and subsequently stirred at room temperature overnight. The reaction mixture was treated with 500 ml of water and extracted four times with 50 ml of hexane each time, the combined organic phases were washed twice with 500 ml of water each time, dried over magnesium sulphate, the suspension was filtered and the filtrate was concentrated. The residue was purified by chromatography on silica gel with hexane and the product obtained was recrystallized from hexane at -78° C. to give 2.4 g of 1-bromo-4-[trans-4-[(E)-3-methoxypropenyl]cyclohexyl]benzene, m.p. (C-I) 47° C.

Workup

  1. stirringsubsequently stirred at room temperature overnight
  2. extractionextracted four times with 50 ml of hexane each time
  3. washthe combined organic phases were washed twice with 500 ml of water each time
  4. dry with materialdried over magnesium sulphate
  5. filtrationthe suspension was filtered
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by chromatography on silica gel with hexane
  8. customthe product obtained
  9. customwas recrystallized from hexane at -78° C.

Sources & evidence

ORD record
ord-7be93d93224f414a8753910edf7b7519
Source dataset
uspto-grants-1994_02
Patent number
US05288428

Reaction notes

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