Carbon Dioxide → HCID 59199292, compound

HRID 2079683Notes

Reaction equation

HRID 2079683 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][C:4]=1[NH:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16].C1(C)C=CC=CC=1.[Li]CCCC.[C:32](=[O:34])=[O:33]>C1COCC1.O>[CH3:1][O:2][C:3]1[C:4]([NH:13][C:14](=[O:19])[C:15]([CH3:16])([CH3:18])[CH3:17])=[C:5]([C:6]([C:9]([F:12])([F:11])[F:10])=[CH:7][CH:8]=1)[C:32]([OH:34])=[O:33]

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 1140TolueneHCID 59199277HCID 59199277, compoundHCID 178418339Butyllithium

Product 1

HCID 59199292HCID 59199292, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-50 °C

Procedure

N-(2-methoxy-5-(trifluoromethyl)phenyl) pivalamide (1 eq) was azeotrope with toluene (x=3). Dissolved in THF, cooled to −50° C. and added n-BuLi (2 eq, 2.5M solution in hexane) dropwise. The reaction mixture was stirred at −50° C. for 1 h then warmed to −10° C. in 30 min. Stirred at this temperature for 30 min then CO2 gas was passed through cylinder into the reaction mixture at −10 to 0° C. for 1 h. The reaction mixture was warmed to room temperature and stirred overnight. The reaction was poured to water and extracted with ethyl acetate. (EtOAc extracts contained starting material). The aq layer pH was adjusted to 1-2 and product was extracted with ethyl acetate (x=3). The ethyl acetate extracts were combined, washed with brine and dried over sodium sulfate.

Workup

  1. temperaturethen warmed to −10° C. in 30 min
  2. stirringStirred at this temperature for 30 min
  3. temperatureThe reaction mixture was warmed to room temperature
  4. stirringstirred overnight
  5. extractionextracted with ethyl acetate
  6. extractionwas extracted with ethyl acetate (x=3)
  7. washwashed with brine
  8. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-e906e6aa291b4805b58909b644c17008
Source dataset
uspto-grants-2011_04
Patent number
US07932262B2

Reaction notes

Loading…