Water → HCID 21838014, compound

HRID 1740290Notes

Reaction equation

HRID 1740290 reaction equation
[C:1]([C:4]1[CH2:8][O:7][CH2:6][C:5]=1[C:9]1[CH:10]=[C:11]([C:15]2[O:16][CH2:17][C:18]([CH3:21])([CH3:20])[N:19]=2)[CH:12]=[CH:13][CH:14]=1)(=O)[NH2:2].O>ClCCl>[C:1]([C:4]1[CH2:8][O:7][CH2:6][C:5]=1[C:9]1[CH:10]=[C:11]([C:15]2[O:16][CH2:17][C:18]([CH3:21])([CH3:20])[N:19]=2)[CH:12]=[CH:13][CH:14]=1)#[N:2]

Participants

4

Reactant 2

HCID 962WaterHCID 21838301HCID 21838301, compound

Product 1

HCID 21838014HCID 21838014, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[3-(4-carbamoyl-2,5-dihydrofuran-3-yl)phenyl]-4,4-dimethyl-4,5-dihydrooxazole (0.1 g) in dichloromethane (1 ml) was added dropwise bis(trifluoromethanesulfonic)anhydride (0.0588 ml) at 0° C. and the mixture was stirred at room temperature for two hours. Then water was added to the reaction mixture and the stirring was continued for thirty minutes. The product was extracted with ethyl acetate and the organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with chloroform. The fractions containing the desired product were collected and evaporated in vacuo to give 2-[3-(4-cyano-2,5-dihydrofuran-3-yl)phenyl]-4,4-dimethyl-4,5-dihydrooxazole.

Workup

  1. waitthe stirring was continued for thirty minutes
  2. extractionThe product was extracted with ethyl acetate
  3. washthe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel eluting with chloroform
  7. additionThe fractions containing the desired product
  8. customwere collected
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-c7da64494777436ea1d8870b93703f7a
Source dataset
uspto-grants-1999_10
Patent number
US05968985

Reaction notes

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