Pyridine → (3-Ethyloxetan-3-yl)methyl 3-pyridinecarboxylate

HRID 345288

Reaction equation

HRID 345288 reaction equation
Cl.[CH2:2](Cl)[C:3]1[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=1.[CH2:10]([C:12]1([CH2:16][OH:17])[CH2:15][O:14][CH2:13]1)[CH3:11].N1C=CC=CC=1.C(=O)([O-])[O-:25].[Na+].[Na+]>ClCCl>[N:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([O:17][CH2:16][C:12]2([CH2:10][CH3:11])[CH2:15][O:14][CH2:13]2)=[O:25])[CH:4]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 10340Sodium CarbonateHCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 76444Oxt-101

Product 1

HCID 19992002(3-Ethyloxetan-3-yl)methyl 3-pyridinecarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Nicotinyl chloride hydrochloride (8.9 gm.) was added to a stirred solution of 3-ethyl-3-hydroxymethyloxetane (5.8 gm.) and dry pyridine (20 ml.) in dry dichloromethane (150 ml.) at 0°. The mixture was stirred at room temperature for 4 days and poured into aqueous sodium carbonate solution. The aqueous mixture was extracted with dichloromethane. The extracts were washed with water and dried over anhydrous magnesium sulphate. The solvent was removed in vacuo. The residue was purified by chromatography on silica eluting with 5% triethylamine in dichloromethane. (3-Ethyloxetan-3-yl)methyl 3-pyridinecarboxylate was obtained as a pale yellow oil (7.0 gm.).

Workup

  1. extractionThe aqueous mixture was extracted with dichloromethane
  2. washThe extracts were washed with water
  3. dry with materialdried over anhydrous magnesium sulphate
  4. customThe solvent was removed in vacuo
  5. customThe residue was purified by chromatography on silica eluting with 5% triethylamine in dichloromethane

Sources & evidence

ORD record
ord-e348c7bc47ba44ad998de5232bb87078
Source dataset
uspto-grants-1991_10
Patent number
US05057504

Linked notes

Loading…