Citric Acid → HCID 69590513, compound
Reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1OCCCO.[H-].[Na+].Br[C:15]1[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][N:16]=1.[C:22](O)(=O)[CH2:23][C:24](CC(O)=O)(C(O)=O)[OH:25]>CN(C=O)C>[Br:21][C:18]1[CH:19]=[CH:20][C:15]([O:25][CH2:24][CH2:23][CH2:22][CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][O:1]2)=[N:16][CH:17]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 3-tetrahydropyranyloxy-1-propanol (1.0 g, 6.25 mmol) in DMF (10.0 mL) was added NaH (0.17 g, 95%) and stirred at 0° C. After 30 minutes, 2,5 dibromopyridine (1.0 g, 4.22 mmol) was added and the mixture was stirred at room temperature for 2 hours. The mixture was then poured into 5% cold citric acid (10.0 mL) and extracted with EtOAc (3×15 mL). The combined organic extracts were washed with water (3×15 mL), dried (Na2SO4), and concentrated to dryness. The resulting material was purified by silica gel flash chromatography using 20% EtOAc in hexane containing 0.5% triethyl amine. The appropriate fractions (monitored by TLC in 30% EtOAc in hexane) were combined and concentrated to give the desired product (1.1 g) as a colorless syrup. 1H-NMR and mass spectral data were consistent with the structure.
Workup
- stirringthe mixture was stirred at room temperature for 2 hours
- extractionextracted with EtOAc (3×15 mL)
- washThe combined organic extracts were washed with water (3×15 mL)
- dry with materialdried (Na2SO4)
- concentrationconcentrated to dryness
- customThe resulting material was purified by silica gel flash chromatography
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-487b3c17856e43af9cfba77613ab90f5
- Source dataset
- uspto-grants-2005_08
- Patent number
- US06933304B2
Reaction notes
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