Benzyl Alcohol → HCID 69692935, compound

HRID 1814372Notes

Reaction equation

HRID 1814372 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9](Cl)=[N:10]2.[CH2:17]([OH:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[H-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O.[N+](=C)=[N-]>C1COCC1.CCOCC.C1(C)C=CC=CC=1.C(O)(=O)C.O.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9]([O:24][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[N:10]2

Participants

12

Reactant 5

HCID 244Benzyl Alcohol2×HCID 311Citric AcidHCID 9550Diazomethane2×HCID 24758Sodium hydrideHCID 86588219HCID 86588219, compound

Product 1

HCID 69692935HCID 69692935, compound

Reagents, catalysts & solvents 6

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

(2-Chloroquinolin-5-yl)-acetic acid methyl ester (0.198 g, 1.01 mmol), whose synthesis was previously described, and benzyl alcohol (0.722 g, 6.67 mmol) were dissolved in anhydrous THF, and NaH (60% in oil, 0.244 g, 6.10 mmol) was added. The reaction was stirred at room temperature overnight. The solution was poured into ethyl acetate and water and the layers were separated. The organic layer was washed twice with water, then washed with brine, dried over magnesium sulfate, filtered and rotovapped to give the excess starting benzyl alcohol. The basic aqueous layer was acidified with 5% citric acid solution and extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and rotovapped. The crude product was dissolved in ether and treated with freshly prepared diazomethane (14 mmol) in ether. The diazomethane solution was treated with acetic acid (1 mL). The solvent was stripped off, toluene was added and stripped off. Traces of toluene were removed by azeotroping with acetonitrile. (2-Benzyloxy-quinolin-5-yl)-acetic acid methy ester was used without further purification. MS m/z 308 (M+1).

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed twice with water
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customto give the
  7. extractionextracted three times with ethyl acetate
  8. washThe combined organic layers were washed with brine
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. dissolutionThe crude product was dissolved in ether
  12. customTraces of toluene were removed
  13. customby azeotroping with acetonitrile
  14. custom(2-Benzyloxy-quinolin-5-yl)-acetic acid methy ester was used without further purification

Sources & evidence

ORD record
ord-c50c5407570f4972be933a14eab82deb
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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