Potassium Carbonate → HCID 12993970, compound

HRID 351798Notes

Reaction equation

HRID 351798 reaction equation
N1[C:5]2([CH2:9][O:8][C:7]([SH:10])=[N:6]2)[CH2:4][O:3]C=1S.Br[CH2:13][CH2:14][C:15]([F:19])=[C:16]([F:18])[F:17].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[OH:3][CH2:4][C:5]1[N:6]=[C:7]([S:10][CH2:13][CH2:14][C:15]([F:19])=[C:16]([F:18])[F:17])[O:8][CH:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 663334-Bromo-1,1,2-trifluorobut-1-eneHCID 178527816HCID 178527816, compound

Product 1

HCID 12993970HCID 12993970, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

7.5 g of 3,8-dioxa-1,6-diazaspiro[4,4]nona-1,6-diene-2,7-dithiol, 7.5 g of 4-bromo-1,1,2-trifluoro-1-butene and 7.0 g of potassium carbonate were added to 200 ml of acetonitrile and refluxed for 5 hours. The reaction mixture was cooled to room temperature and filtered by sucction and the filtrate was distilled under reduced pressure. The residue was purified by column chromatography (eluent: ethyl acetate:dichloromethane=1:4) to obtain 7.0 g of 4-hydroxymethyl-2-(3,4,4-trifluoro-3-butenylthio)oxazole as colorless oil (yield 74.2%). n20D=1.4910.

Workup

  1. temperaturerefluxed for 5 hours
  2. filtrationfiltered by sucction
  3. distillationthe filtrate was distilled under reduced pressure
  4. customThe residue was purified by column chromatography (eluent: ethyl acetate:dichloromethane=1:4)

Sources & evidence

ORD record
ord-8f269912776a4764a54217fd810589f9
Source dataset
uspto-grants-2004_06
Patent number
US06743814B2

Reaction notes

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