Methyl iodide → HCID 57827430, compound

HRID 1842128Notes

Reaction equation

HRID 1842128 reaction equation
[CH2:1]([O:3][CH:4]([O:12][CH2:13][CH3:14])[CH2:5][CH:6]([OH:11])[CH2:7][CH2:8][CH:9]=[CH2:10])[CH3:2].[H-].[Na+].[CH3:17]I.[Cl-].[NH4+]>O.CN(C=O)C>[CH2:13]([O:12][CH:4]([O:3][CH2:1][CH3:2])[CH2:5][CH:6]([O:11][CH3:17])[CH2:7][CH2:8][CH:9]=[CH2:10])[CH3:14]

Participants

7

Reactant 4

HCID 6328Methyl iodide2×HCID 24758Sodium hydride2×HCID 25517Ammonium ChlorideHCID 57827354HCID 57827354, compound

Product 1

HCID 57827430HCID 57827430, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DMF (30 mL) was added to 1,1-diethoxy-hept-6-en-3-ol obtained in Preparation Example 57-(1) (3.07 g), and the mixture was cooled in an ice bath under a nitrogen atmosphere. Then, sodium hydride (60% 699 mg) was added, followed by stirring for 10 minutes. Methyl iodide (1.8 mL, specific gravity: 2.28 g/cm3) was added, followed by stirring for one hour and 50 minutes. Then, the mixture was warmed to room temperature and further stirred for one hour and 30 minutes. Sodium hydride (600, 300 mg) and methyl iodide (0.9 mL, specific gravity: 2.28 g/cm3) were further added, followed by stirring for two hours and 30 minutes. Then, water and a saturated ammonium chloride solution were slowly added, followed by stirring for a while. After extraction with ethyl acetate, the organic layer was sequentially washed with a saturated ammonium chloride solution, water and brine. The resulting organic layer was dried over anhydrous magnesium sulfate. The drying agent was removed by filtration and then the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound (2.98 g).

Workup

  1. temperaturethe mixture was cooled in an ice bath under a nitrogen atmosphere
  2. stirringby stirring for one hour and 50 minutes
  3. stirringfurther stirred for one hour and 30 minutes
  4. stirringby stirring for two hours and 30 minutes
  5. stirringby stirring for a while
  6. extractionAfter extraction with ethyl acetate
  7. washthe organic layer was sequentially washed with a saturated ammonium chloride solution, water and brine
  8. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  9. customThe drying agent was removed by filtration
  10. concentrationthe filtrate was concentrated under reduced pressure
  11. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3b151576288b4d06901801989aec560b
Source dataset
uspto-grants-2015_02
Patent number
US08946211B2

Reaction notes

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