Hydrochloric Acid → HCID 69004882, compound

HRID 230790

Reaction equation

HRID 230790 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([OH:22])=[O:21])=[CH:16][CH:15]=1.[N:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29](OC)=[O:30].Cl>O.C1COCC1.CCCCCC>[O:30]=[C:29]([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][N:23]=1)[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([OH:22])=[O:21])=[CH:16][CH:15]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 7470P-Toluic AcidHCID 7912DiisopropylamineHCID 755692-CarbomethoxypyridineHCID 178418339Butyllithium

Product 1

HCID 69004882HCID 69004882, compoundYield 11.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

A THF solution (50 mL) of diisopropylamine (12.6 mL) was cooled to 0° C., and a hexane (33 mL) solution of 2.6 M n-butyllithium was added thereto and stirred at that temperature for 10 minutes. Then this was cooled to −78° C., and a THF solution (15 mL) of 4-methylbenzenecarboxylic acid (2.3 g) was dropwise added thereto. The reaction liquid was stirred at −40° C. for 2.5 hours, and then a THF solution (4 mL) of methyl picolinate (2.0 g) was dropwise added thereto. The reaction solution was heated up to room temperature, and stirred for one day. Next, water was added to the reaction liquid, then controlled to have a pH of 4 with aqueous hydrochloric acid solution added thereto, and then extracted with ethyl acetate. The organic layer was dried with anhydrous sodium sulfate, concentrated under reduced pressure, and the resulting residue was purified through silica gel column chromatography (hexane/ethyl acetate=4/1) to obtain the entitled compound (400 mg).

Workup

  1. customThe reaction liquid
  2. stirringwas stirred at −40° C. for 2.5 hours
  3. temperatureThe reaction solution was heated up to room temperature
  4. stirringstirred for one day
  5. additionadded
  6. extractionextracted with ethyl acetate
  7. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customthe resulting residue was purified through silica gel column chromatography (hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-8df35751d93e4b309d88ce135b230de5
Source dataset
uspto-grants-2009_07
Patent number
US07566781B2

Linked notes

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