Methyl iodide → HCID 22120011, compound

HRID 1274066Notes

Reaction equation

HRID 1274066 reaction equation
[Cl:1][C:2]1[C:14]([CH:15]([C:17]2[O:18][CH:19]=[CH:20][CH:21]=2)[OH:16])=[C:13]([Cl:22])[CH:12]=[CH:11][C:3]=1[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].[H-].[Na+].I[CH3:26]>O1CCCC1.[Cl-].[Na+]>[Cl:1][C:2]1[C:14]([CH:15]([C:17]2[O:18][CH:19]=[CH:20][CH:21]=2)[O:16][CH3:26])=[C:13]([Cl:22])[CH:12]=[CH:11][C:3]=1[C:4]([O:6][C:7]([CH3:10])([CH3:8])[CH3:9])=[O:5]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22120012HCID 22120012, compound

Product 1

HCID 22120011HCID 22120011, compound

Reagents, catalysts & solvents 2

HCID 5234Sodium ChlorideSolventHCID 8028TetrahydrofuranSolvent

Procedure

At room temperature, 3.0 g (8.8 mmol) of tert-butyl 2,4-dichloro-3-((2-furyl)(hydroxymethyl))benzoate in 40 ml of tetrahydrofuran are stirred for 1 h with 0.4 g (16.6 mmol) of sodium hydride. 6.3 g (43.8 mmol) of iodomethane are added dropwise and the mixture is stirred at room temperature for a further 3 h. The reaction mixture is taken up in 100 ml of saturated aqueous sodium chloride solution, extracted with methyl tert-butyl ether, dried over sodium sulfate, filtered and freed from the solvent under reduced pressure. The crude product is purified by silica gel chromatography using cyclohexane/ethyl acetate. Yield: 2.7 g; 1H NMR, δ [ppm], (CDCl3): 1.6 (s), 3.5 (s), 6.2 (m), 6.3 (m), 7.4 (m), 7.5 (d)

Workup

  1. extractionextracted with methyl tert-butyl ether
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customThe crude product is purified by silica gel chromatography

Sources & evidence

ORD record
ord-faf12742ab9c4bb0a723da49c073386b
Source dataset
uspto-grants-2000_12
Patent number
US06156702

Reaction notes

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