Ethyl propiolate → Ethyl 1-benzyl-1H-pyrrole-3-carboxylate

HRID 51231

Reaction equation

HRID 51231 reaction equation
[CH2:1]([N:8]([CH:13]=O)[CH2:9][C:10](O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15]([O:19][CH2:20][CH3:21])(=[O:18])[C:16]#C>C(OC(=O)C)(=O)C>[CH2:1]([N:8]1[CH:9]=[CH:10][C:16]([C:15]([O:19][CH2:20][CH3:21])=[O:18])=[CH:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 12182Ethyl propiolateHCID 12958481N-benzyl-N-formylglycine

Product 1

HCID 14667729Ethyl 1-benzyl-1H-pyrrole-3-carboxylateYield 94%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

Using 1.93 g (10 mmol) of N-benzyl-N-formylglycine, 3.65 g (37.2 mmol) of ethyl propiolate and 10 ml of acetic anhydride, a reaction and post treatment were conducted in a similar manner as in Referential Example 1. The resulting brown oil was purified by silica gel column chromatography [silica gel: “No.9385”, product of Merck & Co., Inc. (the same silica gel was also used in the subsequent referential examples and examples); eluent: ethyl acetate/hexane=1/3], whereby 2.156 g of the title compound were obtained (yield: 94.0%).

Workup

  1. customa reaction and post treatment
  2. customThe resulting brown oil was purified by silica gel column chromatography [silica gel

Sources & evidence

ORD record
ord-e0fa7bb7423b45bc8f58fa72baab2e22
Source dataset
uspto-grants-2004_03
Patent number
US06713634B2

Linked notes

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