Pyridine → HCID 54190065, compound

HRID 1379812Notes

Reaction equation

HRID 1379812 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([O:14][CH2:15][CH3:16])(OCC)[CH2:9][CH3:10])=[CH:4][CH:3]=1.N1C=CC=CC=1.[O:23](C(C(F)(F)F)=O)[C:24]([C:26]([F:29])([F:28])[F:27])=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:14][CH2:15][CH3:16])=[C:9]([CH3:10])[C:24](=[O:23])[C:26]([F:29])([F:28])[F:27])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 22906421HCID 22906421, compound

Product 1

HCID 54190065HCID 54190065, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

A solution of 2.0 g of 1-chloro-4-(1,1-diethoxypropyl)benzene and 2.5 mL of CH2Cl2 was treated with 1.45 mL of pyridine. The solution was cooled to 0° C. and treated with 5.5 mL of (CF3CO)2O in 2.5 mL of CH2Cl2. After heating overnight at reflux, the reaction mixture was cooled, diluted with CH2Cl2 and 12 mL of ice cold water was added. The organic layer was seperated and washed with 20 mL of 1N HCl, followed by a washing with 20 mL of 10% Na2CO3 and two washings with 20 mL of water. The organic layer was dried over Na2SO4 and concd in vacuo to yield 1.69 g of a dark brown oil. Chromatographic purification (silica, 10% ethyl acetate in hexanes) yielded 1.0 g of a yellow oil. Bulb to bulb distillation gave 0.45 g of a very pure light yellow oil: μ(23,D) 1.5137; major geometric isomer: 1HNMR (CDCl3) δ 1.22 (t, 3H, 7.0 Hz), 1.70 (s, 3H), 3.64 (q, 2H, 7.0 Hz), 7.30 (d, 2H, 8.3 Hz), 7.46 (d, 2H, 8.4 Hz). 19FNMR (CDCl3) δ -74.68 (CF3). Anal. Calcd for C13H12 O2F3Cl: C, 53.35; H, 4.13. Found: C, 53.44; H, 4.10.

Workup

  1. temperatureAfter heating overnight
  2. temperatureat reflux
  3. temperaturethe reaction mixture was cooled
  4. additionwas added
  5. customThe organic layer was seperated
  6. washwashed with 20 mL of 1N HCl
  7. washwashing with 20 mL of 10% Na2CO3 and two washings with 20 mL of water
  8. dry with materialThe organic layer was dried over Na2SO4 and concd in vacuo

Sources & evidence

ORD record
ord-92a111a2b02a4419a7a5885a6ee5ffda
Source dataset
uspto-grants-1997_09
Patent number
US05672715

Reaction notes

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