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cis-1-Bromoheptadec-8-ene → 1-[5-(Pyridin-2-YL)-1,3,4-oxadiazol-2-YL]octadec-9-EN-1-one

HRID 898181
Notes
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Reaction equation

HRID 898181 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[Li]C(C)(C)C.[N:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:30]1[O:34][C:33]([C:35]([O:37]C)=O)=[N:32][N:31]=1>C1COCC1>[N:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:30]1[O:34][C:33]([C:35](=[O:37])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[N:32][N:31]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10710588cis-1-Bromoheptadec-8-eneHCID 59691753Methyl 5-(pyridin-2-yl)-1,3,4-oxadiazole-2-carboxylateHCID 178418306HCID 178418306, compound

Product 1

HCID 673010561-[5-(Pyridin-2-YL)-1,3,4-oxadiazol-2-YL]octadec-9-EN-1-oneYield 23%

Reagents, catalysts & solvents 1

HCID 8028Tetrahydrofuran
Solvent
2×

Procedure

A solution of cis-1-bromo-heptadec-8-ene (60 mg, 0.2 mmol) in THF (1 mL) was treated with t-BuLi (1.5 M in pentane, 270 μL, 0.4 mmol) at −40° C. After stirring for 30 min, the resulting alkyl lithium reagent was added to a solution of methyl 5-(pyridin-2-yl)-[1,3,4]-oxadiazole-2-carboxylate (20 mg, 0.1 mmol) in THF (2 mL) at −40° C. The reaction mixture was stirred for 4 h before it was quenched with the addition of brine. The mixture was extracted with EtOAc, concentrated, and purified by flash chromatography (SiO2, 1×3 cm, 30% EtOAc-hexanes) to provide the title compound (8.5 mg, 23%) as white solid. 1H NMR (400 MHz, CDCl3) 8.85 (dd, J=5, 1.2 Hz, 1H), 8.30 (dd, J=7.9, 1.2 Hz, 1H), 7.94 (td, J=7.6, 1.5 Hz, 1H), 7.54 (ddd, J=7.6, 4.7, 1.2 Hz, 1H), 5.34-5.37 (m, 2H), 3.22 (t, J=7.3 Hz, 2H), 2.02 (m, 4H), 1.82 (m, 2H), 1.27-1.41 (m, 20H), 0.88 (t, J=6.4 Hz, 3H); 13C NMR (CDCl3, 100 MHz) 187.2, 165.1, 161.2, 150.8, 142.6, 150.8, 142.6, 137.3, 130.0, 129.7, 126.7, 124.0, 40.1, 31.9, 29.8, 29.7, 29.5, 29.3, 29.2, 29.1, 29.0, 27.2, 27.1, 23.6, 22.7, 14.1; MALDI-FTMS m/z 412.2955 (C25H37N3O2+H+ requires 412.2958).

Workup

  1. stirringThe reaction mixture was stirred for 4 h before it
  2. customwas quenched with the addition of brine
  3. extractionThe mixture was extracted with EtOAc
  4. concentrationconcentrated
  5. custompurified by flash chromatography (SiO2, 1×3 cm, 30% EtOAc-hexanes)

Sources & evidence

ORD record
ord-83551408447d4f1684c6419546987087
Source dataset
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07351724B2

Reaction notes

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