2-formyl-1-isopropyl-1H-pyrrole-3-carboxylic acid ethyl ester → 2-[(4-chloro-2-methyl-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid ethyl ester

HRID 2204294Notes

Reaction equation

HRID 2204294 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Mg]Br)=[C:4]([CH3:10])[CH:3]=1.[CH2:11]([O:13][C:14]([C:16]1[CH:20]=[CH:19][N:18]([CH:21]([CH3:23])[CH3:22])[C:17]=1[CH:24]=[O:25])=[O:15])[CH3:12]>C1COCC1>[CH2:11]([O:13][C:14]([C:16]1[CH:20]=[CH:19][N:18]([CH:21]([CH3:22])[CH3:23])[C:17]=1[CH:24]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=1[CH3:10])[OH:25])=[O:15])[CH3:12]

Participants

4

Reactant 2

HCID 867030972-formyl-1-isopropyl-1H-pyrrole-3-carboxylic acid ethyl esterHCID 178426105HCID 178426105, compound

Product 1

HCID 867030962-[(4-chloro-2-methyl-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution (0.5 M in THF) of 4-chloro-2-methylphenylmagnesium bromide [480438-47-9] (68.8 mmol) was added to a mixture of 2-formyl-1-isopropyl-1H-pyrrole-3-carboxylic acid ethyl ester (Step A5) (68.8 mmol) in THF (160 mL) at 0° C. After stirring for 2 h, the reaction mixture was quenched with a saturated aqueous solution of NH4Cl and extracted with MTBE (2×). The combined organic phases were successively washed with water and brine, dried (Na2SO4), filtered and concentrated. The residue was suspended in hexanes, stirred for 30 min and then filtered to afford the title compound as a white solid. tR: 7.74 min (HPLC 2); ESI-MS: tR=1.26 min, [M]+318/320 (i.e. fragmented pyrrolium ion) (LC-MS 1); TLC: Rf=0.20 (1:6 EtOAc/hexanes).

Workup

  1. customthe reaction mixture was quenched with a saturated aqueous solution of NH4Cl
  2. extractionextracted with MTBE (2×)
  3. washThe combined organic phases were successively washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. stirringstirred for 30 min
  8. filtrationfiltered

Sources & evidence

ORD record
ord-2d103459bf6e4d4cb11e9af0d68184b6
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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