Sodium Hydroxide → Methyl 1-5-(4-methylbenzoyl)pyrrole-2-acetate

HRID 848043Notes

Reaction equation

HRID 848043 reaction equation
C([C:3]([OH:22])([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)[C:4]1[N:8](C)[C:7]([CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:6][CH:5]=1)#N.[OH-].[Na+]>CCOCC>[CH3:21][C:18]1[CH:17]=[CH:16][C:15]([C:3]([C:4]2[NH:8][C:7]([CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:6][CH:5]=2)=[O:22])=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 12940095Methyl 5-[cyanohydroxy(4-methylphenyl)methyl]-1-methylpyrrole-2-acetate

Product 1

HCID 13041412Methyl 1-5-(4-methylbenzoyl)pyrrole-2-acetateYield 93.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Methyl 5-[cyanohydroxy(4-methylphenyl)methyl]-1-methylpyrrole-2-acetate (0.161 g, 0.540 mmoles) was dissolved in 30 ml of ether and shaken with 10 percent NaOH, washed with brine and dried over MgSO4. Evaporation of the ether yielded 0.130 g (86.1 percent) of methyl 1-5-(4-methylbenzoyl)pyrrole-2-acetate, mp 118°-120°. The IR was identical to an authentic sample of methyl 1-methyl-5-(4-methylbenzoyl)pyrrole-2-acetate.

Workup

  1. washwashed with brine
  2. dry with materialdried over MgSO4
  3. customEvaporation of the ether

Sources & evidence

ORD record
ord-ade4c04787d34bea92389e1d6f82d20b
Source dataset
uspto-grants-1981_10
Patent number
US04294760

Reaction notes

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