Acetamide → HCID 59643453, compound

HRID 2251566Notes

Reaction equation

HRID 2251566 reaction equation
[Br:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([O:8][CH2:9][C:10]([CH:12]2[CH2:14][CH2:13]2)=O)=O)=[CH:4][CH:3]=1.C([NH2:20])(=O)C.B(F)(F)F.CCOCC>>[Br:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]2[O:8][CH:9]=[C:10]([CH:12]3[CH2:14][CH2:13]3)[N:20]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 178AcetamideHCID 8000Boron trifluoride etherateHCID 69099586HCID 69099586, compound

Product 1

HCID 59643453HCID 59643453, compoundYield 16.4%

Procedure

To a mixture of 2-cyclopropyl-2-oxoethyl 4-bromobenzoate (4.51 g, 15.93 mmol) and acetamide (4.71 g, 79.74 mmol) was added BF3/Et2O (1 ml). The mixture was heated at 140C for 8 h. Upon cooling, the mixture was partitioned between water and Et2O. The aqueous phase was extracted with Et2O (1×125 ml). The combined organic phases were washed with Water and brine, dried with MgSO4, and concentrated in vacuo. The crude material was purified by flash chromatography (CH2Cl2/hexanes, 30:70 to 50:50) to yield the title compound as a white crystalline solid (0.69 g, 16%).

Workup

  1. temperatureUpon cooling
  2. customthe mixture was partitioned between water and Et2O
  3. extractionThe aqueous phase was extracted with Et2O (1×125 ml)
  4. washThe combined organic phases were washed with Water and brine
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by flash chromatography (CH2Cl2/hexanes, 30:70 to 50:50)

Sources & evidence

ORD record
ord-d6cc7a7f7a2b4b2a966e60eaa0cc2c36
Source dataset
uspto-grants-2008_01
Patent number
US07319104B2

Reaction notes

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