Acetyl chloride → HCID 12993974, compound

HRID 351802Notes

Reaction equation

HRID 351802 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.C(N(CC)CC)C.[C:23](Cl)(=[O:25])[CH3:24]>ClCCl>[C:23]([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)(=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 12993970HCID 12993970, compound

Product 1

HCID 12993974HCID 12993974, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3 g of 4-hydroxymethyl-2-(3,4,4-trifluoro-3-butenylthio)oxazole and 1.5 g of triethylamine were dissolved in 50 ml of dichloromethane, to which a solution of 1 g of acetyl chloride in 20 ml of dichloromethane was added dropwise under ice cooling. After stirring at room temperature for 8 hours, the mixture was washed with water and dried with anhydrous sodium sulfate. After the solvent was distilled off under reduced pressure, the residue was treated by column chromatography to obtain 2.7 g of 4-acetoxymethyl-2-(3,4,4-trifluoro-3-butenylthio)oxazole (yield 76.5%). n20D=1.4752.

Workup

  1. additionwas added dropwise under ice cooling
  2. washthe mixture was washed with water
  3. dry with materialdried with anhydrous sodium sulfate
  4. distillationAfter the solvent was distilled off under reduced pressure
  5. additionthe residue was treated by column chromatography

Sources & evidence

ORD record
ord-4ebe28b741fe4084bbaa347cbae24c5d
Source dataset
uspto-grants-2004_06
Patent number
US06743814B2

Reaction notes

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