Heptanoyl chloride → HCID 22259667, compound

HRID 1611067Notes

Reaction equation

[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([O:8][CH2:9][CH3:10])=[O:7].[C:11](Cl)(=[O:18])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]>>[C:11]([C:4]1[CH:3]=[C:2]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[NH:1][CH:5]=1)(=[O:18])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

Reactant 2

HCID 17313Heptanoyl chloride

HCID 255670Ethyl 1H-pyrrole-2-carboxylate

Product 1

HCID 22259667HCID 22259667, compoundYield 71.1%

Procedure

Starting with 2.0 g of ethyl pyrrole carboxylate (14 mmol) and 4.2 ml (26 mmol) of heptanoylchloride and following a procedure analogous to the one described above, 2.5 g (70% yield) of the desired product is obtained. 1H NMR (δ ppm, CDCl3): 10.07 (s, br, 1H, NH); 7.53 (dd, J=1.60, 3.35 Hz, 1H, α-pyrrolic); 7.27 (dd, J=1.60, 2.47; 1H; β-pyrrolic); 4.32 (q, 2H, J=7.14 Hz, CO2Et); 2.73 (t, 2H, J=7.50, α-CO CH2); 1.67 (m, 2H, β-CO CH2); 1.33 (t, 3H, J=7.14, CO2Et); 1.28 (m, 6H, γ,δ,ε CH2); 0.85 (m, 3H, end-CH3). 13C NMR (δ ppm, CDCl3): 196.32; 161.26; 127.07; 126.24; 124.01; 114.86; 60.99; 39.78; 31.62; 29.05; 24.59; 22.48; 14.30; 13.99. Exact mass calculated for C14H22NO3 (M+H)=252.159969, found=252.159072.

Sources & evidence

ORD record: ord-fa8087453ed74558852b54dd1aa74497
Source dataset: uspto-grants-2006_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06984734B2

Reaction notes

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