4-Chlorobenzoyl chloride → Ethyl 5-(p-chlorobenzoyl)-3-ethoxycarbonyl-4-hydroxy-1-methylpyrrole-2-acetate

HRID 1388918Notes

Reaction equation

HRID 1388918 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]([OH:11])=[CH:9][N:8]([CH3:12])[C:7]=1[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:5])[CH3:2].[Cl:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1.FC(F)(F)S(O)(=O)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Cl:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([C:9]2[N:8]([CH3:12])[C:7]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[C:10]=2[OH:11])=[O:25])=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 85014-Chlorobenzoyl chlorideHCID 62406Trifluoromethanesulfonic acidHCID 516892Sodium BicarbonateHCID 13345719Ethyl 3-ethoxycarbonyl-4-hydroxy-1-methylpyrrole-2-acetate

Product 1

HCID 135841626Ethyl 5-(p-chlorobenzoyl)-3-ethoxycarbonyl-4-hydroxy-1-methylpyrrole-2-acetateYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 3-ethoxycarbonyl-4-hydroxy-1-methylpyrrole-2-acetate (255 mg, 1.0 mmol) is mixed with p-chlorobenzoyl chloride (385 μl, 3.0 mmol) under nitrogen, and 2.0 ml anhydrous trifluoromethanesulfonic acid is added. The reaction mixture is stirred at room temperature for one hour followed by dilution with methylene chloride (50 ml). Solid sodium bicarbonate is slowly added until the acid is neutralized. The solids are filtered off and washed with an additional 50 ml methylene chloride. The combined methylene chloride solutions are washed with water (20 ml) and saturated brine (50 ml). Subsequently, the washed layers are dried with sodium sulfate and the solvent is removed in vacuo to give a red solid which is recrystallized from ethanol to give 275 mg (70%) of ethyl 5-(p-chlorobenzoyl)-3-ethoxycarbonyl-4-hydroxy-1-methylpyrrole-2-acetate, m.p. 145°-147° C.

Workup

  1. filtrationThe solids are filtered off
  2. washwashed with an additional 50 ml methylene chloride
  3. washThe combined methylene chloride solutions are washed with water (20 ml) and saturated brine (50 ml)
  4. dry with materialSubsequently, the washed layers are dried with sodium sulfate
  5. customthe solvent is removed in vacuo
  6. customto give a red solid which
  7. customis recrystallized from ethanol

Sources & evidence

ORD record
ord-5b3616409e8a4544a053a0733e72d139
Source dataset
uspto-grants-1984_02
Patent number
US04434175

Reaction notes

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