HCID 20464731, compound → HCID 20464715, compound

HRID 325429Notes

Reaction equation

HRID 325429 reaction equation
[CH3:1][N:2]1[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:5]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[CH:15]=2)[CH:4]=[C:3]1[CH2:21][O:22]C(C)(C)C>FC(F)(F)C(O)=O>[CH3:1][N:2]1[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:5]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[CH:15]=2)[CH:4]=[C:3]1[CH2:21][OH:22]

Participants

3

Reactant 1

HCID 20464731HCID 20464731, compound

Product 1

HCID 20464715HCID 20464715, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of ethyl 1-methyl-2-(t-butoxymethyl)-4-(3-methylphenoxymethyl)pyrrole-5-carboxylate (3.82 g, 0.01 mol) is allowed to stand in trifluoroacetic acid (50 ml) at room temperature until all starting material is gone by TLC. The TFA is then removed in vacuo and the residue is stirred for 30 minutes with a saturated solution of sodium carbonate in 50% aqueous ethanol (200 ml). Saturated brine (250 ml) is then added, along with ethyl acetate (250 ml) and the layers are separated. The organic layer is washed twice with H2O (100 ml) then brine (50 ml) and dried over anhydrous sodium sulfate. The solvent is then removed and the residue subjected to preparative HPLC to obtain pure ethyl 1-methyl-2-hydroxymethyl-4-(3-methylphenoxymethyl)pyrrole-5-carboxylate.

Workup

  1. customThe TFA is then removed in vacuo
  2. additionSaturated brine (250 ml) is then added, along with ethyl acetate (250 ml)
  3. customthe layers are separated
  4. washThe organic layer is washed twice with H2O (100 ml)
  5. dry with materialbrine (50 ml) and dried over anhydrous sodium sulfate
  6. customThe solvent is then removed

Sources & evidence

ORD record
ord-8858500ba6134c799a818a733f2a28ab
Source dataset
uspto-grants-1984_04
Patent number
US04440779

Reaction notes

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