Triethylamine → 3-[(4-Phenoxyphenyl)sulfonyl]propan-1-al

HRID 849548Notes

Reaction equation

HRID 849548 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([S:14]([CH2:17][CH2:18][CH2:19][OH:20])(=[O:16])=[O:15])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.C(OCC)(=O)C>C(Cl)Cl.CS(C)=O>[O:1]([C:8]1[CH:13]=[CH:12][C:11]([S:14]([CH2:17][CH2:18][CH:19]=[O:20])(=[O:16])=[O:15])=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 193668023-[(4-Phenoxyphenyl)sulfonyl]propan-1-ol

Product 1

HCID 193668353-[(4-Phenoxyphenyl)sulfonyl]propan-1-alYield 101.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

Part D: A cooled solution of 13 g (44 mmol) of 3-[(4-phenoxyphenyl)sulfonyl]propan-1-ol from Part C in 60 mL of anhydrous CH2Cl2 was treated with 25 mL (18 g, 178 mM) of triethylamine. The reaction mixture was then treated with a slurry of 28 g (178 mM) of pyridine-SO3 complex in 60 mL of methyl sulfoxide added over one-half hour. After stirring for one hour, the reaction mixture was poured over 500 mL of ice and ethyl acetate was added. The layers were separated and the organic layer was washed with 5% KHSO4 solution, water and brine, dried (MgSO4), and concentrated to afford 13 g of 3-[(4-phenoxyphenyl)sulfonyl]propan-1-al, suitable for the next reaction.

Workup

  1. additionadded over one-half hour
  2. additionwas added
  3. customThe layers were separated
  4. washthe organic layer was washed with 5% KHSO4 solution, water and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-95f76c4cc4724f5e836b53b9c2b62600
Source dataset
uspto-grants-2000_01
Patent number
US06013649

Reaction notes

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