Chlorodifluoromethane → HCID 18696206, compound

HRID 1739063Notes

Reaction equation

HRID 1739063 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][N:8]=[C:7]([O:10][CH2:11][CH2:12][NH:13]C(OC(C)(C)C)=O)[C:6]=2[CH:21]=1.C[O-].[Na+].[Cl:25][CH:26]([F:28])[F:27]>CN(C)C=O>[ClH:25].[NH2:13][CH2:12][CH2:11][O:10][C:7]1[C:6]2[CH:21]=[C:2]([O:1][CH:26]([F:28])[F:27])[CH:3]=[CH:4][C:5]=2[O:9][N:8]=1

Participants

5

Reactant 3

HCID 6372ChlorodifluoromethaneHCID 10942334Sodium MethoxideHCID 18696107HCID 18696107, compound

Product 1

HCID 18696206HCID 18696206, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-hydroxy-3-(2-(N-t-butoxycarbonylamino)ethoxy)-1,2-benzisoxazole (100 mg) in dimethylformamide (4 ml) was added sodium methoxide (90 mg) and the mixture was stirred at room temperature for 10 minutes, then followed by introduction of chlorodifluoromethane gas for 20 minutes. The reaction mixture was poured into ice water (30 ml), extracted with ethyl acetate (twice each with 30 ml) and the combined extracts were dried over anhydrous magnesium sulphate and filtered. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography with cyclohexane/ethyl acetate (9/1) as an eluent, to give the title compound (19 mg, 16%) as a colorless powder.

Workup

  1. extractionextracted with ethyl acetate (twice each with 30 ml) and the combined extracts
  2. dry with materialwere dried over anhydrous magnesium sulphate
  3. filtrationfiltered
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography with cyclohexane/ethyl acetate (9/1) as an eluent

Sources & evidence

ORD record
ord-3fdb5ca5ea424430aab26cadbbf00b50
Source dataset
uspto-grants-1999_10
Patent number
US05965591

Reaction notes

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