Dimethylformamide → HCID 69665687, compound

HRID 1160280Notes

Reaction equation

HRID 1160280 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH:5]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21](OC)=[CH:20][CH:19]=2)=[CH:12][CH:11]=1)[CH2:6][C:7]#[C:8][CH3:9])[CH3:2].[CH3:27]C1C=CC=CC=1CBr.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C=O)C>C(O)(=O)C>[CH2:1]([O:3][C:4](=[O:26])[CH:5]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[CH3:27])=[CH:12][CH:11]=1)[CH2:6][C:7]#[C:8][CH3:9])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6992o-Xylyl bromideHCID 10796Cesium carbonateHCID 69665419HCID 69665419, compound

Product 1

HCID 69665687HCID 69665687, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

Ester 15.1 (3.19 g, 9 mmol) was taken up in glacial acetic acid (100 mL) in a 250 mL RB Flask, and the suspension was heated to reflux for 16 h. The solvent was removed under reduced pressure, and the residue was re-dissolved in ethyl acetate (200 mL). The solution was washed with 1 N HCl(aq) (200 mL) and saturated brine (200 mL), dried over MgSO4 and concentrated to a thick yellow oil, to which was added 2-methylbenyl bromide (2.57 g, 13.9 mmol), cesium carbonate (6.03 g, 18.5 mmol) and DMF (20 mL). The suspension was heated to 80° C. for overnight. After cooling, the reaction was quenched with water (200 mL) and extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with NaHCO3 (sat. 2×100 mL), and NaCl (sat. 3×100 mL), dried over MgSO4, and concentrated to a white powder (2.41 g, 79%).

Workup

  1. temperaturethe suspension was heated
  2. temperatureto reflux for 16 h
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe residue was re-dissolved in ethyl acetate (200 mL)
  5. washThe solution was washed with 1 N HCl(aq) (200 mL) and saturated brine (200 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated to a thick yellow oil, to which
  8. temperatureAfter cooling
  9. customthe reaction was quenched with water (200 mL)
  10. extractionextracted with ethyl acetate (2×100 mL)
  11. washThe combined organic layers were washed with NaHCO3 (sat. 2×100 mL), and NaCl (sat. 3×100 mL)
  12. dry with materialdried over MgSO4
  13. concentrationconcentrated to a white powder (2.41 g, 79%)

Sources & evidence

ORD record
ord-80803d2127c5495c9438342e93747f38
Source dataset
uspto-grants-2010_10
Patent number
US07816367B2

Reaction notes

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