Methyl iodide → HCID 19384250, compound

HRID 2399729Notes

Reaction equation

HRID 2399729 reaction equation
[F:1][C:2]([F:17])=[CH:3][CH2:4][CH2:5][S:6][C:7]1[O:8][C:9]2[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[C:10]=2[N:11]=1.IC.[C:20](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[F:17][C:2]([F:1])=[CH:3][CH2:4][CH2:5][S:6][C:7]1[O:8][C:9]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:20])[C:10]=2[N:11]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 19384309HCID 19384309, compound

Product 1

HCID 19384250HCID 19384250, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 2-(4,4-difluorobut-3-enylthio)-4-hydroxy benzoxazole (Compound No. 82, Example 4B(iii), 504mg) in acetone (10 cm3) was added iodomethane (278 mg) and potassium carbonate (270 mg). The reaction mixture was stirred at the ambient temperature for 51/2 hours, then allowed to stand at the ambient temperature for 18 hours. Gc analysis indicated complete consumption of starting material. The reaction mixture was poured into ethyl acetate and and water, the layers separated and the aqueous phase extracted twice with ethyl acetate. The combined organic layers were washed with water, brine, dried (MgSO4) and evaporated under reduced pressure to a yellow oil. Purification by silica-gel chromatography using 5% ethyl acetate in hexane as the eluent gave 2-(4,4-difluorobut-3-enylthio)-4-methoxy-benzoxazole as a colourless oil (290 mg). 1H NMR (CDCl3) δ7.19(1H,t); 7.08(1H,d); 6.78(1H,d); 4.30(1H,ddt); 3.39(1H,t); 2.55(q).

Workup

  1. waitto stand at the ambient temperature for 18 hours
  2. customconsumption of starting material
  3. additionThe reaction mixture was poured into ethyl acetate and and water
  4. customthe layers separated
  5. extractionthe aqueous phase extracted twice with ethyl acetate
  6. washThe combined organic layers were washed with water, brine
  7. dry with materialdried (MgSO4)
  8. customevaporated under reduced pressure to a yellow oil
  9. customPurification by silica-gel chromatography

Sources & evidence

ORD record
ord-d659d309be2b405fbf93c95a83c4a8c9
Source dataset
uspto-grants-1995_09
Patent number
US05451594

Reaction notes

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