Methyl iodide → HCID 23503590, compound

HRID 1835430Notes

Reaction equation

HRID 1835430 reaction equation
O1CCC[CH2:2]1.[CH3:6][O:7][C:8]1[C:13]([O:14][CH3:15])=[C:12]([O:16][CH3:17])[CH:11]=[C:10]([CH3:18])[C:9]=1[CH:19]([C:21]1[C:26]([Br:27])=[CH:25][N:24]=[CH:23][C:22]=1Br)[OH:20].C([Li])CCC.CI>O>[CH3:6][O:7][C:8]1[C:13]([O:14][CH3:15])=[C:12]([O:16][CH3:17])[CH:11]=[C:10]([CH3:18])[C:9]=1[CH:19]([C:21]1[C:22]([CH3:2])=[CH:23][N:24]=[CH:25][C:26]=1[Br:27])[OH:20]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 23503601HCID 23503601, compoundHCID 178418339Butyllithium

Product 1

HCID 23503590HCID 23503590, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A tetrahydrofuran (15 ml) solution of 2.0 g (4.6 mmol) of (2,3,4-trimethoxy-6-methylphenyl)(3,5-dibromo-4-pyridyl)methanol obtained in step (a) was cooled to −78° C., 6.0 ml (9.4 mmol) of n-butyllithium (1.56 M hexane solution) was dropwise added thereto, followed by stirring for 5 minutes, and 0.5 ml (8.0 mmol) of methyl iodide was added thereto, followed by stirring for 2.5 hours. 20 ml of water was added, and tetrahydrofuran was distilled off under reduced pressure. The aqueous layer was extracted with ethyl acetate, the organic layer was dried over anhydrous sodium sulfate and subjected to filtration, and the solvent was distilled off under reduced pressure. The crude product thus obtained was purified by silica gel column chromatography to obtain 0.44 g (yield 25%) of (2,3,4-trimethoxy-6-methylphenyl)(3-bromo-5-methyl-4-pyridyl)methanol.

Workup

  1. stirringby stirring for 2.5 hours
  2. distillationtetrahydrofuran was distilled off under reduced pressure
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. filtrationsubjected to filtration
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe crude product thus obtained
  8. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9d39eff7b3ce4a508c462e9812552a76
Source dataset
uspto-grants-2004_08
Patent number
US06770662B2

Reaction notes

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