Acetic Anhydride → Ethyl 1-ethyl-3-pyrrolecarboxylate

Reaction equation

[CH:1]([N:3]([CH2:5][C:6](O)=O)[CH3:4])=O.[C:9]([O:13][CH2:14][CH3:15])(=[O:12])[C:10]#[CH:11].C(OC(=O)C)(=O)C>>[CH2:5]([N:3]1[CH:1]=[CH:11][C:10]([C:9]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4]1)[CH3:6]

Participants

Reactant 3

HCID 7918Acetic Anhydride

HCID 12182Ethyl propiolate

HCID 11789184N-formylsarcosine

Product 1

HCID 22738058Ethyl 1-ethyl-3-pyrrolecarboxylateYield 71.3%

Procedure

Using 117.1 g (1 mol) of N-formylsarcosine, 98.1 g (1 mol) of ethyl propiolate and 638 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 distilled under reduced pressure and a 103-104° C. fraction was collected under 4 mmHg, whereby 109.19 g of the title compound were obtained (yield: 71.3%).

Workup

customa reaction and post treatment
distillationThe resulting brown oil was distilled under reduced pressure and a 103-104° C. fraction
customwas collected under 4 mmHg

Sources & evidence

ORD record: ord-1623653c25854ecbb75fa271bd9a9811
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06713634B2

Reaction notes

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