Decanoyl chloride → HCID 11197355, compound

HRID 1444766Notes

Reaction equation

HRID 1444766 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:27])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>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:27])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[N:3][CH:4]=1

Participants

7

Reactant 3

HCID 66982Decanoyl chlorideHCID 7371945-(2-Pyridyl)oxazoleHCID 178418339Butyllithium

Product 1

HCID 11197355HCID 11197355, compoundYield 40%

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

(187) A solution of 2-(oxazol-5-yl)pyridine (100 mg, 0.68 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, 0.75 mmol, 0.30 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, 0.68 mmol, 130 mg) was added, and the solution was stirred for 10 min at 0° C. Decanoyl chloride (2 equiv, 1.4 mmol, 270 mg, 0.29 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)decan-1-one (187) (80 mg, 0.27 mmol, 40% yield) as a light brown powder: mp 56-57° C.; 1H NMR (CDCl3, 250 MHz) d 8.69-8.62 (m, 1H), 7.87-7.75 (m, 3H), 7.33-7.25 (m, 1H), 3.08 (t, J=7.7 Hz, 2H), 1.81-1.69 (m, 2H), 1.41-1.19 (m, 12H), 0.86 (br t, J=7.0 Hz, 3H); 13C NMR (CDCl3, 62.5 MHz) d 188.5, 157.3, 153.1, 150.0, 146.2, 136.9, 127.8, 124.1, 120.3, 39.1, 31.8, 29.4, 29.3, 29.2, 29.1, 24.0, 22.6, 14.0; IR (KBr) umax 2930, 2845, 1697, 1601, 1422, 1380 cm−1; MALDI-FTMS (DHB) m/z300.1911 (C18H24N2O2+H+ requires 301.1910).

Workup

  1. stirringstirred for 45 min at 0° C
  2. additionCul (1.0 equiv, 0.68 mmol, 130 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-824f0512c20b4454b712ecc54c89c84f
Source dataset
uspto-grants-2010_02
Patent number
US07662971B2

Reaction notes

Loading…