Dimethylformamide → HCID 58481111, compound

HRID 1625698Notes

Reaction equation

HRID 1625698 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.Br[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([O:1][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:3][C:4]=1[N+:11]([O-:13])=[O:12])(=[O:10])[CH3:9]

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 7748Ethyl bromoacetate2×HCID 11430Potassium Carbonate2×HCID 29939889HCID 29939889, compound2×

Product 1

HCID 58481111HCID 58481111, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

1-(4-Hydroxy-2-nitrophenyl)ethanone (Carbocore, 181 mg, 1.00 mmol), ethyl 2-bromoacetate (183 mg, 1.10 mmol), potassium carbonate (138 mg. 1.00 mmol) and DMF (5 mL) were combined in a 20 mL glass vial and stirred at 60° C. for 2 hours, at which point LC-MS analysis showed a clean complete reaction. The reaction mixture was diluted with water and extracted with EtOAc, washed with sat. NaCl aq. The reaction was repeated using 1-(4-Hydroxy-2-nitrophenyl)ethanone (0.802 g, 4.43 mmol), ethyl 2-bromoacetate (0.813 g, 4.87 mmol), potassium carbonate (0.612 g. 4.43 mmol) and DMF (25 mL), and worked up in the same way. The combined EtOAc extracts were dried over anhydrous MgSO4, filtered and concentrated under reduced pressure, affording ethyl 2-(4-acetyl-3-nitrophenoxy)acetate (TU3205-034) as a dark yellow oil MS (ESI+): calcd. 268.07. found 268.10 (MH+). H-NMR (400 MHz, CDCl3): 1.317 (3H, t, J=7.2 Hz), 2.512 (3H, s), 4.294 (2H, q, J=7.2 Hz), 4.722 (2H, s), 7.192 (1H, dd, J=8.4 Hz, 2.4 Hz), 7.455 (1H, d, J=8.4 Hz), 7.462 (1H, d, J=2.8 Hz). C-NMR (100 MHz, CDCl3): 14.133, 29.695, 61.922, 65.499, 110.105, 119.735, 129.461, 130.154, 147.793, 159.356, 167.474, 198.352.

Workup

  1. customa clean complete reaction
  2. extractionextracted with EtOAc
  3. washwashed with sat. NaCl aq. The reaction
  4. dry with materialThe combined EtOAc extracts were dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fd9c0fe6f4b345e9a599c62bdaa8d9b1
Source dataset
uspto-grants-2014_07
Patent number
US08785151B2

Reaction notes

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