Dimethyl Sulfoxide → HCID 21278446, compound

HRID 649042Notes

Reaction equation

HRID 649042 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH2:12][C:13]1[CH:17]=[CH:16][N:15]([CH2:18][C:19]#[CH:20])[C:14]=1[C:21]#[N:22].C(N(CC)CC)C>C(Cl)Cl.O>[CH:12]([C:13]1[CH:17]=[CH:16][N:15]([CH2:18][C:19]#[CH:20])[C:14]=1[C:21]#[N:22])=[O:11]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 13605017HCID 13605017, compound

Product 1

HCID 21278446HCID 21278446, compoundYield 42.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent4×

Procedure

27 ml of a 1M solution of oxalyl chloride in methylene chloride were cooled to -60° C. and 13.5 ml of a 1M solution of dimethyl sulfoxide in methylene chloride were added. After stirring for 5 minutes, a solution of 1.09 g of 3-hydroxymethyl-1-(2-propynyl)-1H-pyrrole-2-carbonitrile in 20 ml of methylene chloride was added, and the temperature was kept at -60° C. for 2 hours. 70 ml of a 1M solution of triethylamine in methylene chloride were added with stirring for 10 minutes at -60° C., and the temperature was allowed to rise to 20° C. 20 ml of water were added, followed by stirring, decanting and concentrating to dryness. The residue was chromatographed over silica and eluted with a mixture of hexane and ethyl acetate (6-4) to obtain 456 mg of 3-formyl-2-cyano-1-(2-propynyl)-1H-pyrrole.

Workup

  1. waitthe temperature was kept at -60° C. for 2 hours
  2. stirringwith stirring for 10 minutes at -60° C.
  3. customto rise to 20° C
  4. stirringby stirring
  5. customdecanting
  6. concentrationconcentrating to dryness
  7. customThe residue was chromatographed over silica
  8. washeluted with a mixture of hexane and ethyl acetate (6-4)

Sources & evidence

ORD record
ord-4385c53fa8914476aadf9b2bcec8fb15
Source dataset
uspto-grants-1988_04
Patent number
US04737513

Reaction notes

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