Water → HCID 86654670, compound

HRID 880451Notes

Reaction equation

HRID 880451 reaction equation
C(N(CC)CC)C.[OH:8][CH2:9][CH2:10][N:11]1[CH:15]=[C:14]([I:16])[CH:13]=[C:12]1[CH:17]=[O:18].[CH3:19][C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1.O>ClCCl>[CH3:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([O:8][CH2:9][CH2:10][N:11]2[CH:15]=[C:14]([I:16])[CH:13]=[C:12]2[CH:17]=[O:18])(=[O:28])=[O:27])=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 86654669HCID 86654669, compound

Product 1

HCID 86654670HCID 86654670, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Triethylamine (3.3 mL, 23.8 mmol) was added to a stirred solution of 1-(2-hydroxyethyl)-4-iodo-pyrrole-2-carbaldehyde (2.1 g, 7.92 mmol) in dichloromethane (15 mL). The reaction mixture was chilled to 0° C. and 4-methyl-benzenesulfonyl chloride (1.82 g, 9.51 mmol) was added over 15 min. The reaction mixture was allowed to warm to ambient temperature and stirred overnight. Water was added, the organic phase separated and the aqueous phase extracted with dichloromethane. The combined organic layers were washed with saturated sodium bicarbonate solution, brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give a residue which was purified by washing with petroleum ether to afford 2-(2-formyl-4-iodo-pyrrol-1-yl)ethyl 4-methylbenzenesulfonate (2.4 g, 72%) as a grey solid.

Workup

  1. temperatureto warm to ambient temperature
  2. customthe organic phase separated
  3. extractionthe aqueous phase extracted with dichloromethane
  4. washThe combined organic layers were washed with saturated sodium bicarbonate solution, brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give a residue which
  8. customwas purified
  9. washby washing with petroleum ether

Sources & evidence

ORD record
ord-41dcd71045b84862af91ec56ada9932a
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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