Citric Acid → HCID 68533576, compound

HRID 1436909Notes

Reaction equation

HRID 1436909 reaction equation
[Mg].II.Br[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH3:11].C[O:13][C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1.[CH:20]([O:22][CH:23](Cl)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[CH2:23]([O:22][C:20]([N:17]1[CH:18]=[CH:19][C:14](=[O:13])[CH2:15][CH:16]1[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH3:11])=[O:21])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

8

Reactant 6

HCID 311Citric AcidHCID 807IodineHCID 72362-BromotolueneHCID 692784-MethoxypyridineHCID 5462224MagnesiumHCID 18761384HCID 18761384, compound

Product 1

HCID 68533576HCID 68533576, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent4×

Conditions

Temperature
-40 °C

Procedure

To 20 ml of tetrahydrofuran were added 1.34 g of magnesium and trace of iodine, and added dropwise thereto was a solution of 9.50 g of 2-bromotoluene in 45 ml of tetrahydrofuran, to prepare Grignard reagent. To the Grignard reagent was added dropwise a solution of 5.46 g of 4-methoxypyridine in 20 ml of tetrahydrofuran under nitrogen atmosphere at −60° C. or below. Subsequently, a solution of 10.24 g of chlorobenzyl formate in 50 ml of tetrahydrofuran was added dropwise thereto at −40° C. and the mixture was stirred for 3 hours. The temperature of the mixture was raised to room temperature and added thereto was 120 ml of a 5% aqueous citric acid solution. The mixture was extracted with ethyl acetate and washed with saturated brine. The organic layer was dried and concentrated under reduced pressure. The residue was crystallized with diisopropyl ether, and the crystals were collected by filtration, to give 11.15 g of 1-benzyloxycarbonyl-2-(2-methylphenyl)-4-oxo-3,4-dihydro-2H-pyridine.

Workup

  1. additionadded dropwise
  2. temperatureThe temperature of the mixture was raised to room temperature
  3. additionadded
  4. extractionThe mixture was extracted with ethyl acetate
  5. washwashed with saturated brine
  6. customThe organic layer was dried
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was crystallized with diisopropyl ether
  9. filtrationthe crystals were collected by filtration

Sources & evidence

ORD record
ord-4e451ce5de8d4018933dfbac4bbd4f01
Source dataset
uspto-grants-2009_11
Patent number
US07619092B2

Reaction notes

Loading…