Methyl iodide → HCID 178500378, compound

HRID 507844Notes

Reaction equation

HRID 507844 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]([C@H:7]1[CH2:12][CH2:11][C@@H:10]([OH:13])[CH2:9][CH2:8]1)([CH3:6])[CH3:5].[H-].[Na+].[CH3:17]I>O1CCCC1>[CH3:1][O:2][C:3](=[O:14])[C:4]([C@H:7]1[CH2:8][CH2:9][C@@H:10]([O:13][CH3:17])[CH2:11][CH2:12]1)([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178500376HCID 178500376, compound

Product 1

HCID 178500378HCID 178500378, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

0.500 g of 2-(cis-4-hydroxy-cyclohexyl)-2-methyl-propionic acid methyl ester (Example 87b) are dissolved in 5 ml of dry tetrahydrofuran. 0.120 g of sodium hydride (60% dispersion) is added in portions and the mixture stirred at 40° C. for 1 hour. Methyl iodide (0.233 ml) is added and the mixture heated to 40° C. for 5 hours. The reaction mixture is then cooled to room temperature, quenched with 5 ml of water and extracted with tert-butyl methyl ether (2×50 ml). The combined organic phases are dried over sodium sulphate and concentrated by evaporation. The title compound is identified from the residue by means of flash chromatography (SiO2 60F) based on its Rf value.

Workup

  1. temperaturethe mixture heated to 40° C. for 5 hours
  2. temperatureThe reaction mixture is then cooled to room temperature
  3. customquenched with 5 ml of water
  4. extractionextracted with tert-butyl methyl ether (2×50 ml)
  5. dry with materialThe combined organic phases are dried over sodium sulphate
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-2709f457d7fa4b6d9285d7e26820f906
Source dataset
uspto-grants-2010_08
Patent number
US07786307B2

Reaction notes

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