Hydrochloric Acid → HCID 12993971, compound

HRID 351799Notes

Reaction equation

HRID 351799 reaction equation
[OH:1][CH2:2][C:3]1[N:4]=[C:5]([S:8][CH2:9][CH2:10][C:11]([F:15])=[C:12]([F:14])[F:13])[O:6][CH:7]=1.[H-].[Na+].[CH3:18]I.Cl>O1CCCC1>[CH3:18][O:1][CH2:2][C:3]1[N:4]=[C:5]([S:8][CH2:9][CH2:10][C:11]([F:15])=[C:12]([F:14])[F:13])[O:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 12993970HCID 12993970, compound

Product 1

HCID 12993971HCID 12993971, compoundYield 52.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 2.7 g of 4-hydroxymethyl-2-(3,4,4-trifluoro-3-butenylthio)oxazole in 50 ml of tetrahydrofuran (dehydrated) was added dropwise to a suspension of 0.5 g NaH (purity about 60%) in 20 ml of tetrahydrofuran (dehydrated) at 0° C. After stirring the mixture at room temperature for 1 hour, a solution of 2.0 g of methyl iodide in 20 ml of tetrahydrofuran (dehydrated) was added at 0° C. and further stirred at room temperature for 1 hour. The reaction mixture was poured into a mixed solution of 200 g ice and 2N hydrochloric acid. After extraction with 100 ml of dichloromethane, the solution was washed with water and dried with anhydrous magnesium sulfate. After the solvent was distilled off under reduced pressure, the residue was purified by column chromatography (eluent: dichloromethane) to obtain 1.5 g of 4-methoxymethyl-2-(3,4,4-trifluoro-3-butenylthio)oxazole as colorless oil (yield 52.5%). n20D=1.4710.

Workup

  1. stirringfurther stirred at room temperature for 1 hour
  2. extractionAfter extraction with 100 ml of dichloromethane
  3. washthe solution was washed with water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. distillationAfter the solvent was distilled off under reduced pressure
  6. customthe residue was purified by column chromatography (eluent: dichloromethane)

Sources & evidence

ORD record
ord-4433565374f54faeb9a53d2762197b27
Source dataset
uspto-grants-2004_06
Patent number
US06743814B2

Reaction notes

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