Acetic Acid → HCID 18614742, compound

HRID 1265184Notes

Reaction equation

HRID 1265184 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[CH:17]=[C:16]2[CH2:18][CH:19]([F:22])[CH:20]([F:21])[C:15]2=[N:14]1.C(O)(=[O:25])C>[O-2].[Cr+6].[O-2].[O-2]>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[CH:17]=[C:16]2[C:18](=[O:25])[CH:19]([F:22])[CH:20]([F:21])[C:15]2=[N:14]1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 18614745HCID 18614745, compound

Product 1

HCID 18614742HCID 18614742, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 10219390chromium (VI) trioxideCatalyst

Conditions

Temperature
50 °C

Procedure

To a solution of (86) (20.2 mg, 56.6 mmol) in 500 mL acetic acid was added chromium(VI) oxide (30 mg, 283 mmol). The mixture was stirred at 50° C. for 12 h. The solvent was removed under reduced pressure. The mixture was then chromatographed on a silica gel TLC plate using hexane/ethyl acetate (9:1) to give (87): Yield 76%): 1H NMR (400 MHz, CDCl3) δ 7.97 (s, 1H), 7.81 (s, 2H), 6.23 (dd, 1H, J=4.97, 55.81 Hz), 5.37 (ddd, 1H, J=4.97, 12.36, 47.15 Hz).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe mixture was then chromatographed on a silica gel TLC plate

Sources & evidence

ORD record
ord-ae1dd3035d62493999a3c628a0c783d4
Source dataset
uspto-grants-2003_04
Patent number
US06545033B1

Reaction notes

Loading…