Ethanol → 5-(benzo[c][1,2,5]oxadiazol-5-yl)-2,2-dimethylfuran-3(2H)-one

HRID 1258320Notes

Reaction equation

HRID 1258320 reaction equation
[N:1]1[O:2][N:3]=[C:4]2[CH:9]=[C:8]([C:10](=[O:17])[C:11]#[C:12][C:13](O)([CH3:15])[CH3:14])[CH:7]=[CH:6][C:5]=12.C(NCC)C.C([OH:25])C>>[N:1]1[O:2][N:3]=[C:4]2[CH:9]=[C:8]([C:10]3[O:17][C:13]([CH3:14])([CH3:15])[C:12](=[O:25])[CH:11]=3)[CH:7]=[CH:6][C:5]=12

Participants

4

Reactant 3

HCID 702Ethanol2×HCID 8021DiethylamineHCID 593548531-(Benzo[c][1,2,5]oxadiazol-5-yl)-4-hydroxy-4-methylpent-2-yn-1-one

Product 1

HCID 593548355-(benzo[c][1,2,5]oxadiazol-5-yl)-2,2-dimethylfuran-3(2H)-oneYield 83%

Procedure

To a stirred solution of 1-(benzo[c][1,2,5]oxadiazol-5-yl)-4-hydroxy-4-methylpent-2-yn-1-one (0.3 g, 1.304 mmol) in ethanol (15 mL), a solution of diethyl amine (0.095 g, 1.304 mmol) in EtOH (5 mL) was added dropwise at RT. The reaction mixture was then stirred for 2 h. The ethanol was then removed, and the mixture was diluted with EtOAc (10 mL). The combined organic layers were washed with water (5 mL) and brine (10 mL), dried over Na2SO4, filtered, and concentrated in vacuo to afford 5-(benzo[c][1,2,5]oxadiazol-5-yl)-2,2-dimethylfuran-3(2H)-one (0.25 g, 83%) as a black oil.

Workup

  1. customThe ethanol was then removed
  2. additionthe mixture was diluted with EtOAc (10 mL)
  3. washThe combined organic layers were washed with water (5 mL) and brine (10 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dabf2980f46c4bafa94185f0c6791428
Source dataset
uspto-grants-2013_06
Patent number
US08466148B2

Reaction notes

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