Acetamide → HCID 59643131, compound

HRID 2251561Notes

Reaction equation

HRID 2251561 reaction equation
[CH:1]1([C:4]([O:6][CH2:7][C:8]([C:10]2[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][CH:11]=2)=O)=O)[CH2:3][CH2:2]1.C([NH2:20])(=O)C.B(F)(F)F.CCOCC>O>[Br:16][C:13]1[CH:14]=[CH:15][C:10]([C:8]2[N:20]=[C:4]([CH:1]3[CH2:3][CH2:2]3)[O:6][CH:7]=2)=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 178AcetamideHCID 8000Boron trifluoride etherateHCID 69099704HCID 69099704, compound

Product 1

HCID 59643131HCID 59643131, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2-(4-bromophenyl)-2-oxoethyl cyclopropane carboxylate (6.00 g, 21.19 mmol) and acetamide (6.60 g, 111.73 mmol) was added BF3/Et2O (4 ml). The mixture was heated to 140C for 2.5 h. Upon cooling, water was added, and the mixture was extracted with Et2O (4×125 ml). The combined organic phases were dried with MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (CH2Cl2/hexanes, 7:3) to provide the title compound as a yellow solid (3.61 g, 64%).

Workup

  1. temperatureUpon cooling
  2. extractionthe mixture was extracted with Et2O (4×125 ml)
  3. dry with materialThe combined organic phases were dried with MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by flash chromatography (CH2Cl2/hexanes, 7:3)

Sources & evidence

ORD record
ord-070d5c6ec19e484abfed74ae974d1a64
Source dataset
uspto-grants-2008_01
Patent number
US07319104B2

Reaction notes

Loading…