Dimethylformamide → HCID 66651992, compound

HRID 418912Notes

Reaction equation

HRID 418912 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]1[CH2:15][C:16]([OH:18])=O.C(Cl)(=O)C(Cl)=O.ClCCl.CN(C=O)C>Cl[Ti](Cl)(Cl)Cl.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:4]=1[CH:9]1[CH:10]([CH2:15][C:16]2=[O:18])[CH2:11][CH2:12][CH2:13][CH2:14]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 66651942HCID 66651942, compound

Product 1

HCID 66651992HCID 66651992, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Combine [2-(2-methoxy-phenyl)-cyclohexyl]-acetic acid (0.300 g, 1.21 mmol), oxalyl chloride (0.13 mL, 1.45 mmol), and dichloromethane (6.0 mL) and catalytic DMF (0.1 mL) at room temperature. After 1 hour at 0° C. added TiCl4 (0.33 mL, 3.0 mmol) and reaction gradually warmed to room temperature. After 3 hours, quenched reaction with 5N HCl and added ethyl acetate. Separate layers, wash with brine, and dry over anhydrous sodium sulfate. Concentrate and flash chromatograph using 0 to 20% ethyl acetate/hexanes eluent to yield the titled compound (0.198 g, 72%). TLC Rf=0.4 in 20% ethyl acetate/hexanes. 1H NMR (CDCl3): 7.6 (d, 1H, J=7.0 Hz), 7.3 (m, 1H), 7.0 (m, 1H), 3.8 (s, 3H), 3.2 (m, 1H), 2.9 (m, 1H), 2.4 (m, 2H), 1.9 (m, 1H), 1.6 (m, 7H).

Workup

  1. customat room temperature
  2. additionAfter 1 hour at 0° C. added
  3. customquenched
  4. customreaction with 5N HCl
  5. washSeparate layers, wash with brine
  6. dry with materialdry over anhydrous sodium sulfate
  7. concentrationConcentrate

Sources & evidence

ORD record
ord-4fbaac0d19b84b41bf2f6b9273249f44
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

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