Methyl iodide → HCID 10808426, compound

HRID 376387Notes

Reaction equation

HRID 376387 reaction equation
[Si:1]([O:8][C:9]1[C:18]2[C:17](=[O:19])[O:16][C:15]([CH2:20][C:21]#[N:22])=[CH:14][C:13]=2[CH:12]=[C:11]([O:23][CH3:24])[CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH-].[Na+].[F-].[CH2:28]([N+](CCCC)(CCCC)CCCC)CCC.CI>C(Cl)Cl>[Si:1]([O:8][C:9]1[C:18]2[C:17](=[O:19])[O:16][C:15]([CH:20]([C:21]#[N:22])[CH3:28])=[CH:14][C:13]=2[CH:12]=[C:11]([O:23][CH3:24])[CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 6328Methyl iodide2×HCID 14798Sodium HydroxideHCID 2724141Tetrabutylammonium FluorideHCID 10545487HCID 10545487, compound

Product 1

HCID 10808426HCID 10808426, compoundYield 155.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

2.50 g (7.24 mmol) of the 8-tert-butyldimethylsilyloxy-3-cyanomethyl-6-methoxy-1-oxo-1H-2-benzopyran obtained in Example 5 was dissolved in 80 ml of methylene chloride. 100 ml of a 1M aqueous solution of sodium hydroxide was added thereto, and the resulting mixture was cooled to 0° C. While this mixture was being vigorously stirred, 584 mg (1.81 mmol) of tetrabutylammonium fluoride and then 10 ml of methylene chloride containing 0.92 ml (14.47 mmol) of methyl iodide were added thereto, followed by stirring at 0° C. for 1 hour. Moreover, 10 ml of methylene chloride containing 0.92 ml (14.47 mmol) of methyl iodide was added thereto, followed by stirring for 30 minutes. After completion of the reaction, the methylene chloride layer was separated, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography [using 130 g of Wako Gel C-200 and hexane/ethyl acetate (5:1)]. Thus, 1.01 g of the title compound was obtained in a 39% yield.

Workup

  1. stirringby stirring at 0° C. for 1 hour
  2. stirringby stirring for 30 minutes
  3. customAfter completion of the reaction
  4. customthe methylene chloride layer was separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography [using 130 g of Wako Gel C-200 and hexane/ethyl acetate (5:1)]

Sources & evidence

ORD record
ord-5cdfd2ee95a7463a9f3660463e8ea93e
Source dataset
uspto-grants-2000_02
Patent number
US06020363

Reaction notes

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