Benzyl Alcohol → 1-[6-(Benzyloxy)pyridin-3-yl]cyclopropanecarboxylic acid

HRID 557857Notes

Reaction equation

HRID 557857 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]2([C:11]([O:13]CC)=[O:12])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH2:16]([OH:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[H-].[Na+]>C(OCC)(=O)C>[CH2:16]([O:23][C:2]1[N:7]=[CH:6][C:5]([C:8]2([C:11]([OH:13])=[O:12])[CH2:9][CH2:10]2)=[CH:4][CH:3]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydride2×HCID 86602273Ethyl 1-(6-chloropyridin-3-yl)cyclopropanecarboxylate

Product 1

HCID 666616601-[6-(Benzyloxy)pyridin-3-yl]cyclopropanecarboxylic acid

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of ethyl 1-(6-chloropyridin-3-yl)cyclopropanecarboxylate (45.1 mg, 0.000200 mol), benzyl alcohol (0.50 mL, 0.0048 mol) and sodium hydride (9.50 mg, 0.000238 mol) was irradiated by microwave at 150° C. for 15 minutes. After cooling, additional sodium hydride (9.5 mg) was added to the mixture. The mixture then was irradiated by microwave at 150° C. for 15 minutes. Ethyl acetate (5 mL) was added and the resulting mixture was washed with water and brine successively. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by Combiflash with ethyl acetate/hexane to give the desired product.

Workup

  1. customwas irradiated by microwave at 150° C. for 15 minutes
  2. temperatureAfter cooling
  3. customThe mixture then was irradiated by microwave at 150° C. for 15 minutes
  4. washthe resulting mixture was washed with water and brine successively
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by Combiflash with ethyl acetate/hexane

Sources & evidence

ORD record
ord-250de9df8d3545d59d6186c5fe27e56a
Source dataset
uspto-grants-2011_11
Patent number
US08058288B2

Reaction notes

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