Trifluoromethanesulfonic acid → Ethyl 5-[o-(chloromethyl)benzoyl]-3-ethoxycarbonyl-4-hydroxy-1-methylpyrrole-2-acetate

HRID 325410Notes

Reaction equation

HRID 325410 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][CH2:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23](Cl)=[O:24].FC(F)(F)S(O)(=O)=O.C(=O)(O)[O-].[Na+]>O.C(Cl)Cl>[Cl:19][CH2:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23]([C:9]1[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]=1[OH:11])=[O:24]

Participants

7

Reactant 4

HCID 62406Trifluoromethanesulfonic acidHCID 516892Sodium BicarbonateHCID 30163952-(Chloromethyl)benzoyl chlorideHCID 13345719Ethyl 3-ethoxycarbonyl-4-hydroxy-1-methylpyrrole-2-acetate

Product 1

HCID 135721047Ethyl 5-[o-(chloromethyl)benzoyl]-3-ethoxycarbonyl-4-hydroxy-1-methylpyrrole-2-acetateYield 64.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Ethyl 3-ethoxycarbonyl-4-hydroxy-1-methylpyrrole-2-acetate (510 mg, 2.0 mmol) is mixed with o-(chloromethyl)benzoyl chloride (565 μl, 4.0 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), and then water (30 ml). Solid sodium bicarbonate is slowly added until the acid is neutralized. The organic layer is separated and the aqueous layer is washed with methylene chloride (50 ml). The combined organic layers 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 525 mg (64.5%) of ethyl 5-[o-(chloromethyl)benzoyl]-3-ethoxycarbonyl-4-hydroxy-1-methylpyrrole-2-acetate.

Workup

  1. customThe organic layer is separated
  2. washthe aqueous layer is washed with methylene chloride (50 ml)
  3. washThe combined organic layers 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-26e922afd6bf42df8d51e63accb5f0d2
Source dataset
uspto-grants-1984_04
Patent number
US04440779

Reaction notes

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