Palmitoyl chloride → HCID 11383548, compound

HRID 1444763Notes

Reaction equation

HRID 1444763 reaction equation
[O:1]1[C:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=2)=[CH:4][N:3]=[CH:2]1.[Li]CCCC.[C:17](Cl)(=[O:33])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]>C1COCC1.CCOC(C)=O.[Cl-].[Cl-].[Zn+2]>[N:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[C:5]1[O:1][C:2]([C:17](=[O:33])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[N:3][CH:4]=1

Participants

7

Reactant 3

HCID 8206Palmitoyl chlorideHCID 7371945-(2-Pyridyl)oxazoleHCID 178418339Butyllithium

Product 1

HCID 11383548HCID 11383548, compoundYield 42%

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

(183) A solution of 2-(oxazol-5-yl)pyridine (95 mg, 0.65 mmol) in anhydrous THF (5 mL) cooled to −75° C. under N2 was treated with n-BuLi (2.5 M in hexanes, 1.1 equiv, 0.72 mmol, 0.29 mL), and stirred for 20 min. ZnCl2 (0.5 M in THF, 2.0 equiv, 1.30 mmol, 2.6 mL) was added at −75° C., and stirred for 45 min at 0° C. Cul (1.0 equiv, 0.65 mmol, 124 mg) was added, and the solution was stirred for 10 min at 0° C. Palmitoyl chloride (2 equiv, 1.3 mmol, 357 mg, 0.39 mL) was added and the solution was stirred for 1 h at 0° C. The reaction was diluted with EtOAc (10 mL), and washed with 15% aqueous NH4OH (1×10 mL), H2O (1×10 mL), and saturated aqueous NaCl (1×10 mL). The organic layer was dried (Na2SO4), filtered, and concentrated under reduced pressure. Flash chromatography (SiO2, 2.5 cm×17.5 cm, 20% EtOAc-hexanes) afforded 1-(5-(pyridin-2-yl)oxazol-2-yl)hexadecan-1-one (183) (103 mg, 0.27 mmol, 42% yield) as an off-white powder: mp 78-80° C.; 1H NMR (CDCl3, 250 MHz) d 8.66 (br d, J=5.1 Hz, 1H), 7.88-7.76 (m, 3H), 7.34-7.27 (m, 1H), 3.10 (t, J =7.3 Hz, 2H), 1.83-1.70 (m, 2H), 1.24 (br s, 24H), 0.87 (br t, J=6.9 Hz, 3H); 13C NMR (CDCl3, 62.5 MHz) d 188.6, 157.4, 153.2, 150.1, 146.3, 137.0, 126.8, 124.1, 120.4, 39.2, 31.9, 29.6 (2C), 29.6 (2C), 29.4 (2C), 29.3 (3C), 29.2 24.0, 22.7, 14.1; IR (KBr) umax 2935, 2847, 1699, 1605, 1425, 1381 cm−1; MALDI-FTMS (DHB) m/z 385.2841 (C24H36N2O2+H+ requires 385.2849).

Workup

  1. stirringstirred for 45 min at 0° C
  2. additionCul (1.0 equiv, 0.65 mmol, 124 mg) was added
  3. stirringthe solution was stirred for 10 min at 0° C
  4. stirringthe solution was stirred for 1 h at 0° C
  5. washwashed with 15% aqueous NH4OH (1×10 mL), H2O (1×10 mL), and saturated aqueous NaCl (1×10 mL)
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4fece8d9e4c0474c9e065108033e87c8
Source dataset
uspto-grants-2010_02
Patent number
US07662971B2

Reaction notes

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