Water → HCID 19858048, compound

HRID 2073399Notes

Reaction equation

HRID 2073399 reaction equation
[CH3:1][C:2]1([CH3:32])[C:6](=[O:7])[O:5][C:4]2[CH:8]=[CH:9][C:10]3[C:15]([C:3]1=2)=[CH:14][C:13]([CH:16](OS(C1C=CC(C)=CC=1)(=O)=O)[C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=3.[NH:33]1[CH:37]=[N:36][CH:35]=[N:34]1.O>S1(=O)(=O)CCCC1>[CH3:1][C:2]1([CH3:32])[C:6](=[O:7])[O:5][C:4]2[CH:8]=[CH:9][C:10]3[C:15]([C:3]1=2)=[CH:14][C:13]([CH:16]([N:33]1[CH:37]=[N:36][CH:35]=[N:34]1)[C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=3

Participants

5

Reactant 3

HCID 962WaterHCID 92571H-1,2,4-TriazoleHCID 19858084HCID 19858084, compound

Product 1

HCID 19858048HCID 19858048, compound

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Procedure

A solution of 1,1-dimethyl-8-(2,2,2-trifluoro-1-tosyloxyethyl)-2(1H)-naphtho[2,1-b]furanone and 1,2,4-triazole (0.5 g) in tetrahydrothiophen-1,1-dioxide (1 ml) was heated at 140° for 18 h. The mixture was treated with water (20 ml) and extracted twice with diethyl ether, and the combined ether extracts were dried and evaporated to dryness under reduced pressure. The residue was purified by flash chromatography, using ethyl acetate: pentane, 1:1 v/v, as eluant, to give 1,1-dimethyl-8-[1-(1H-1,2,4-triazol-1-yl)-2,2,2-trifluoroethyl]-2(1H)-naphtho[2,1-b]furanone. Nmr in deuteriochloroform: δ 8.35(1H,s); 8.15(1H,d); 8.09(1H,s); 7.98(1H,d); 7.87(1H,d); 7.51(1H,dd); 7.46(1H,d); 6.14(1H,q); 1.78(3H,s); 1.75(3H,s).

Workup

  1. extractionextracted twice with diethyl ether
  2. dry with materialthe combined ether extracts were dried
  3. customevaporated to dryness under reduced pressure
  4. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-0970ef7bc4114b12b116ef4ad5ebdac8
Source dataset
uspto-grants-1990_04
Patent number
US04916148

Reaction notes

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