Dodecanoyl chloride → HCID 11450288, compound

HRID 1444765Notes

Reaction equation

HRID 1444765 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:29])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>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:29])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[N:3][CH:4]=1

Participants

7

Reactant 3

HCID 8166Dodecanoyl chlorideHCID 7371945-(2-Pyridyl)oxazoleHCID 178418339Butyllithium

Product 1

HCID 11450288HCID 11450288, compoundYield 53%

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

(185) A solution of 2-(oxazol-5-yl)pyridine (102 mg, 0.70 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, 0.77 mmol, 0.31 mL), and stirred for 20 min. ZnCl2 (0.5 M in THF, 2.0 equiv, 1.40 mmol, 2.8 mL) was added at −75° C., and stirred for 45 min at 0° C. Cul (1.0 equiv, 0.70 mmol, 133 mg) was added, and the solution was stirred for 10 min at 0° C. Lauroyl chloride (2 equiv, 1.4 mmol, 306 mg, 0.32 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)dodecan-1-one (185) (122 mg, 0.37 mmol, 53% yield) as an off-white powder: mp 73-74° C.; 1H NMR (CDCl3, 250 MHz) d 8.65 (br d, J=4.0 Hz, 1H), 7.89-7.75 (m, 3H), 7.34-7.25 (m, 1H), 3.09 (t, J =7.7 Hz, 2H), 1.83-1.69 (m, 2H), 1.41-1.19 (m, 16H), 0.86 (br t, J=7.0 Hz, 3H); 13C NMR (CDCl3, 62.5 MHz) d 188.6, 153.2, 150.1 (2C), 146.3, 137.1, 126.8, 124.1, 120.3, 39.1, 31.9, 29.6 (2C), 29.4, 29.3, 29.2 (2C), 24.0, 22.7, 14.1; IR (KBr) umax 2929, 2857, 1704, 1609, 1415, 1378 cm−1; MALDI-FTMS (DHB) m/z 329.2214 (C20H28N2O2+H+ requires 329.2223).

Workup

  1. stirringstirred for 45 min at 0° C
  2. additionCul (1.0 equiv, 0.70 mmol, 133 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-febdb97ab836477f9472fcf5de69a3f4
Source dataset
uspto-grants-2010_02
Patent number
US07662971B2

Reaction notes

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