Triethylamine → HCID 19366861, compound

HRID 849538Notes

Reaction equation

HRID 849538 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH2:12][CH2:13][CH2:14]S)(=[O:11])=[O:10])=[CH:5][CH:4]=1.C(N(CC)CC)C.C(OCC)(=[O:25])C>C(Cl)Cl.CS(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH2:12][CH2:13][CH:14]=[O:25])(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 18411961HCID 18411961, compound

Product 1

HCID 19366861HCID 19366861, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

Part A: To a solution of 5.2 g (23 mmol) of 3-[(4-methoxyphenyl)sulfonyl]propan-1-ol from Example 13 and 12.6 mL (9.1 g, 90 mmole) of triethylamine in 25 mL of methylene chloride at zero° C., was added a solution of 14.4 g (90 mmol) of sulfur trioxide-pyridine complex in 25 mL of DMSO. After 1 hour, the reaction mixture was added to 200 mL of ice, ethyl acetate was added, the organic layer was separated and washed with water, 5% potassium hydrogen sulfate solution and brine, dried with magnesium sulfate, filtered and concentrated to afford 4.9 g of 3-[(4-methoxyphenyl)sulfonyl]propan-1-al suitable for the next reaction.

Workup

  1. additionwas added
  2. customthe organic layer was separated
  3. washwashed with water, 5% potassium hydrogen sulfate solution and brine
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f3d793d114b94996aae0c4e56bfbdda2
Source dataset
uspto-grants-2000_01
Patent number
US06013649

Reaction notes

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