Acetic Acid → HCID 20464731, compound

HRID 325428Notes

Reaction equation

HRID 325428 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][CH:27]=1)[O:5][CH2:6][C:7]([CH:9]=[C:10]([N:17]([CH3:24])[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:11][O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=O.[O-]CC.[Na+].C(O)(=O)C>C(O)C.C(OCC)(=O)C>[CH3:24][N:17]1[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:7]([CH2:6][O:5][C:4]2[CH:25]=[CH:26][CH:27]=[C:2]([CH3:1])[CH:3]=2)[CH:9]=[C:10]1[CH2:11][O:12][C:13]([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 2723922Sodium ethoxideHCID 53982270HCID 53982270, compound

Product 1

HCID 20464731HCID 20464731, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(3-methylphenoxyacetyl)-2-(N-ethoxycarbonylmethyl-methylamino)-3-t-butoxy-1-propene (40 g, 0.1 mol) in absolute ethanol (250 ml) is added sodium ethoxide (1.0 g, 0.015 mol) under N2. The reaction is stirred at room temperature and monitored by TLC until all starting material has disappeared. Then acetic acid (0.9 g, 0.015 mole) is added and the mixture taken to dryness in vacuo. The residue is dissolved in ethyl acetate (200 ml) and washed with water (100 ml), then saturated brine (100 ml) and dried over anhydrous sodium sulfate. The solvent is removed and the crude product is purified by preparative HPLC to afford pure ethyl 1-methyl-2-(t-butoxymethyl)-4-(3-methylphenoxymethyl)pyrrole-5-carboxylate

Workup

  1. washwashed with water (100 ml)
  2. dry with materialsaturated brine (100 ml) and dried over anhydrous sodium sulfate
  3. customThe solvent is removed
  4. customthe crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-e11c2fa0f5ad4ca88e947c60d6e68a2e
Source dataset
uspto-grants-1984_04
Patent number
US04440779

Reaction notes

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