Dodecanoyl chloride → HCID 22259666, compound

HRID 1611068Notes

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:23])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>>[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:23])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

Reactant 2

HCID 8166Dodecanoyl chloride

HCID 255670Ethyl 1H-pyrrole-2-carboxylate

Product 1

HCID 22259666HCID 22259666, compoundYield 33.1%

Procedure

Starting with 10.0 g of ethyl pyrrole carboxylate (72 mmol) and 33 ml (144 mmol) of dodecanoylchloride and following a procedure analogous to the one described above, 7.65 g (33% yield) of the desired product is obtained. 1H NMR (δ ppm, CDCl3): 9.66 (s, br, 1H, NH); 7.51 (dd, J=1.61, 3.40; 1H, α-pyrrolic); 7.26 (dd, J=1.61, 2.60; 1H ; β-pyrrolic); 4.33 (q, 2H, J=7.16 Hz, CO2Et); 2.73 (t, 2H, J=7.53; α-CO CH2); 1.68 (m, 2H, β-CO CH2); 1.35 (t, 3H, J=7.16; CO2Et); 1.23 (m, 16H, alkyl-CH2); 0.85 (t, 3H, J=7.02, end CH3). 13C NMR (δ ppm, CDCl3): 196.21; 160.96; 127.19; 125.88; 124.09; 114.68; 60.92; 39.81; 31.89; 29.60; 29.58; 29.49; 29.45; 29.41; 29.31; 24.62; 22.66; 14.34; 14.08. Exact mass calculated for C19H32NO3 (M+H)=322.238219, found=322.238983.

Sources & evidence

ORD record: ord-5543cdb4bece456bbb433a93d92ca5d6
Source dataset: uspto-grants-2006_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06984734B2

Reaction notes

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