Triethylamine → 1-(2-Hex-5-ynoylperhydropyridazinyl)-3,3-dimethylpentane-1,2-dione

HRID 2228458

Reaction equation

HRID 2228458 reaction equation
[C:1](O)(=[O:7])[CH2:2][CH2:3][CH2:4][C:5]#[CH:6].C(N(CC)CC)C.ClC(OCC(C)C)=O.[CH3:24][C:25]([CH3:38])([CH2:36][CH3:37])[C:26](=[O:35])[C:27]([CH:29]1[CH2:34][CH2:33][CH2:32][NH:31][NH:30]1)=[O:28]>C(Cl)Cl>[C:1]([N:30]1[CH:29]([C:27](=[O:28])[C:26](=[O:35])[C:25]([CH3:38])([CH3:24])[CH2:36][CH3:37])[CH2:34][CH2:33][CH2:32][NH:31]1)(=[O:7])[CH2:2][CH2:3][CH2:4][C:5]#[CH:6]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 1430365-Hexynoic acidHCID 694178043,3-Dimethyl-1-perhydropyridazinylpentane-1,2-dione

Product 1

HCID 184700651-(2-Hex-5-ynoylperhydropyridazinyl)-3,3-dimethylpentane-1,2-dioneYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-hexynoic acid (0.467 g, 4 mmol) in 10 ml CH2Cl2 was added triethylamine (0.56 ml, 4 mmol), followed by isobutyl chloroformate (0.53 ml, 4 mmol) at 0° C. After stirring for 5 minutes, a solution of 3,3-dimethyl-1-perhydropyridazinyl pentane-1,2-dione (0.424 g, 2 mmol) in 1 ml CH2Cl2 was added. The reaction was gradually warmed up to room temperature. The crude material was subject to silica gel purification to yield final product as clear oil (0.385 g, 63%). 1H NMR (CDCl3, 400 MHz) δ 0.91 (t, 3H, J=7.0); 1.26 (s, 6H); 1.76(m, 8H); 2.28 (m, 2H); 2.50 (m, 2H); 2.88 (m, 2H); 3.60 (m, 1H); 4.50 (m, 2H).

Workup

  1. customThe crude material was subject to silica gel purification

Sources & evidence

ORD record
ord-cff6e2b7d0f34adfafed6d40de6e5289
Source dataset
uspto-grants-2002_07
Patent number
US06417189B1

Linked notes

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