Triethylamine → HCID 18536105, compound

HRID 412142Notes

Reaction equation

HRID 412142 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[CH2:5][N:6]1[C:10]([CH2:11][OH:12])=[CH:9][N:8]=[CH:7]1.C(N(CC)CC)C.CCOC(C)=O>CS(C)=O>[I:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[CH2:5][N:6]1[C:10]([CH:11]=[O:12])=[CH:9][N:8]=[CH:7]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 18536147HCID 18536147, compound

Product 1

HCID 18536105HCID 18536105, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of the alcohol from Step B (ca. 10.4 mmol) in 100 mL of DMSO at room temperature was added triethylamine (14.5 mL, 104 mmol), then SO3-pyridine complex (8.27 g, 52 mmol). After 40 minutes, the reaction was poured into EtOAc, washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo to provide the aldehyde as an oily solid contaminated with triethylamine.

Workup

  1. washwashed with water and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5a29241129154bf39a684a0a86de1a53
Source dataset
uspto-grants-2003_05
Patent number
US06562823B1

Reaction notes

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