4,4,4-Trifluoro-1-(2-furanyl)-1,3-butanedione → HCID 59843261, compound

HRID 2196535Notes

Reaction equation

HRID 2196535 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([NH:8][NH2:9])[CH:5]=[CH:6][CH:7]=1.[F:10][C:11]([F:23])([F:22])[C:12](=O)[CH2:13][C:14]([C:16]1[O:17][CH:18]=[CH:19][CH:20]=1)=O>C(O)(=O)C>[O:17]1[CH:18]=[CH:19][CH:20]=[C:16]1[C:14]1[N:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([I:1])[CH:3]=2)[N:9]=[C:12]([C:11]([F:10])([F:22])[F:23])[CH:13]=1

Participants

4

Reactant 2

HCID 675944,4,4-Trifluoro-1-(2-furanyl)-1,3-butanedioneHCID 2736665(3-Iodophenyl)hydrazine

Product 1

HCID 59843261HCID 59843261, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred suspension of 61 (3.63 g, 8.57 mmol) in acetic acid (34 mL) was added 4,4,4-trifluoro-1-(2-furyl)-1,3-butanedione (1.3 mL, 8.57 mmol). The resulting suspension was allowed to stir at 120° C. overnight turning clear upon heating. The mixture was then evaporated to dryness. The crude product was added to a silica gel column and eluted with 5% to 10% EtOAc/hexanes. The title product 62 (3.00 g, 87% yield) was isolated as a colorless oil that solidified upon standings. LRMS (ESI): calc. 404.1; found 405.2 (MH)+.

Workup

  1. temperatureupon heating
  2. customThe mixture was then evaporated to dryness
  3. additionThe crude product was added to a silica gel column
  4. washeluted with 5% to 10% EtOAc/hexanes

Sources & evidence

ORD record
ord-6b6242de359e405cb0a11de19f98ff3b
Source dataset
uspto-grants-2012_12
Patent number
US08338437B2

Reaction notes

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