Dimethyl Sulfoxide → 4-(2-tert-Butyl-5-nitro-phenyl)-but-3-enal

HRID 2247206Notes

Reaction equation

HRID 2247206 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1[CH:14]=[CH:15][CH2:16][CH2:17][OH:18])([CH3:4])([CH3:3])[CH3:2].C(Cl)(=O)C(Cl)=O.CS(C)=O.[NH4+].[Cl-]>C(Cl)Cl.O>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1[CH:14]=[CH:15][CH2:16][CH:17]=[O:18])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 25517Ammonium ChlorideHCID 65578Oxalyl chlorideHCID 66688391HCID 66688391, compound

Product 1

HCID 738566804-(2-tert-Butyl-5-nitro-phenyl)-but-3-enal

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-78 °C

Procedure

4-(2-tert-Butyl-5-nitro-phenyl)-but-3-en-1-ol (1.024 g) was dissolved in 10 ml of CH2Cl2 and added dropwise over 5 min to a −78° C. mix of oxalyl chloride (0.645 ml), DMSO (0.583 ml), and 10 ml CH2Cl2. The reaction was stirred at −78° C. for 1 h, then treated with a solution of TEA (1.52 ml) in 7 ml CH2Cl2 and stirred at −78° C. for an additional 25 min, then warmed to −30° C. for 35 min. The reaction was treated with 50 ml of saturated aqueous NH4Cl, diluted with H2O and extracted with EtOAc. The organic layer was brine-washed, dried over Na2SO4, filtered, and concentrated in vacuo to yield a yellow oil.

Workup

  1. additionadded dropwise over 5 min to a −78° C.
  2. stirringstirred at −78° C. for an additional 25 min
  3. temperaturewarmed to −30° C. for 35 min
  4. extractionextracted with EtOAc
  5. washwashed
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto yield a yellow oil

Sources & evidence

ORD record
ord-f12560e94711496ab664ad6480d5fcc4
Source dataset
uspto-grants-2010_03
Patent number
US07687643B2

Reaction notes

Loading…