Acetic Anhydride → HCID 21883678, compound

HRID 722318Notes

Reaction equation

HRID 722318 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[N:22]O)[C:5]2[O:10][CH:9]([C:11]([F:14])([F:13])[F:12])[C:8]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:7][C:6]=2[CH:20]=1.C(OC(=O)C)(=O)C>O>[Cl:1][C:2]1[CH:3]=[C:4]([C:21]#[N:22])[C:5]2[O:10][CH:9]([C:11]([F:12])([F:14])[F:13])[C:8]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:7][C:6]=2[CH:20]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 76543197HCID 76543197, compound

Product 1

HCID 21883678HCID 21883678, compoundYield 193.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The oxime from Step 1 (0.61 g, 1.7 mmol) and acetic anhydride (6 mL) were stirred at 140 ° C. for 6.3 hours. The reaction was poured into water, extracted with ethyl acetate, washed with saturated NaHCO3, brine, dried over MgSO4, and concentrated in vacuo to give a brown oil (1.09 g). The oil was purified by flash chromatography (10:1; hexanes: ethyl acetate) yielding upon concentration the title compound as a white solid (0.51 g, 88%): mp 114.6–115.6° C. 1H NMR (CDCl3/300 MHz) 7.65 (s, 1H), 7.53 (d, 1H, J=2.4 Hz), 7.44 (d, 1H, J=2.4 Hz), 5.87 (q, 1H, J=6.4 Hz), 4.36 (m, 2H), 1.37 (t, 3H, J=6.5 Hz).

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with saturated NaHCO3, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-741dc01476004bb5bcc86e436211c5ea
Source dataset
uspto-grants-2006_11
Patent number
US07138411B2

Reaction notes

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