Dimethyl Sulfoxide → HCID 20464723, compound

HRID 325430Notes

Reaction equation

HRID 325430 reaction equation
CS(C)=O.[C:5](Cl)(=[O:9])[C:6](Cl)=O.[CH3:11][C:12]1[CH:13]=[C:14]([CH:25]=[CH:26][CH:27]=1)[O:15][CH2:16][C:17]1[CH:18]=[CH:19][NH:20][C:21]=1[C:22]([O-:24])=[O:23].[CH2:28](N(CC)CC)[CH3:29]>C(Cl)Cl>[CH3:19][N:20]1[C:21]([C:22]([O:24][CH2:28][CH3:29])=[O:23])=[C:17]([CH2:16][O:15][C:14]2[CH:25]=[CH:26][CH:27]=[C:12]([CH3:11])[CH:13]=2)[CH:18]=[C:6]1[CH:5]=[O:9]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 86739347HCID 86739347, compound

Product 1

HCID 20464723HCID 20464723, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of dimethylsulfoxide (390 mg, 5 mmol) in methylene chloride (25 ml) under N2 cooled to -78° C. is added a solution of oxalyl chloride (630 mg, 5 mmol) in methylene chloride (2 ml). The mixture is allowed to stir at -78° for 30 minutes, then a solution of ethyl 1-methyl-2-hydroxymethyl)-4-(3-methylphenoxymethyl)pyrrole-5-carboxylate (1.63 g, 5 mmol) in CH2Cl2 (5 ml) is added. The resulting solution is stirred for 1 hour, then triethylamine (500 mg, 5 mmol) is added. The reaction is followed by TLC until complete. The resulting solution is washed with water (2×25 ml) then saturated brine, and dried over anhydrous sodium sulfate. The crude product is purified by preparative HPLC to afford ethyl 1-methyl-2-formyl-4-(3-methylphenoxymethyl)pyrrole-5-carboxylate.

Workup

  1. stirringThe resulting solution is stirred for 1 hour
  2. washThe resulting solution is washed with water (2×25 ml)
  3. dry with materialsaturated brine, and dried over anhydrous sodium sulfate
  4. customThe crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-f1500e2a996f493894efd8dcc38ea6d1
Source dataset
uspto-grants-1984_04
Patent number
US04440779

Reaction notes

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