Triethylamine → HCID 21835210, compound

HRID 1741279Notes

Reaction equation

HRID 1741279 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH:9]([CH3:12])[CH2:10][OH:11].C(N(CC)CC)C.N1C=CC=CC=1.S(=O)(=O)=O>CS(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH:9]([CH3:12])[CH:10]=[O:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 168533Sulfur trioxide-pyridine2×HCID 21835191HCID 21835191, compound

Product 1

HCID 21835210HCID 21835210, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirred solution of 2-(2,6-dichlorophenyl)propan-1-ol (278 mg, 1.4 mmol) in DMSO (6 ml) was added triethylamine (1.1 ml, 8.1 mmol) followed by pyridine-sulphur trioxide (322 mg, 2.0 mmol). After 1 h more pyridine-sulphur trioxide (161 mg, 1.0 mmol) was added and the mixture stirred for a further 1 h. The mixture was partitioned between EtOAc (3×20 ml) and water (20 ml). The combined organic layers were washed with brine (20 ml) then separated and dried (Na2SO4). The solvent was evaporated and the residue azeotroped with toluene (2×20 ml). The aldehyde was used directly without further purification. 1H NMR (250 MHz, CDCl3) δ 1.51 (3H, d, J=7.0 Hz), 4.17 (1H, q, J=7.0 Hz), 7.20 (1H, t, J=8.0 Hz), 7.33 (2H, d, J=8.5 Hz).

Workup

  1. customThe mixture was partitioned between EtOAc (3×20 ml) and water (20 ml)
  2. washThe combined organic layers were washed with brine (20 ml)
  3. customthen separated
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was evaporated
  6. customthe residue azeotroped with toluene (2×20 ml)
  7. customThe aldehyde was used directly without further purification

Sources & evidence

ORD record
ord-88878070262b4638a00cf5494e0ed274
Source dataset
uspto-grants-1999_10
Patent number
US05973156

Reaction notes

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