Water → 4-Ethyl-1-(3-pyridyl)-2,6,7-trioxabicyclo[2.2.2]octane

HRID 345289

Reaction equation

HRID 345289 reaction equation
B(F)(F)F.CCOCC.[N:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([O:18][CH2:19][C:20]2([CH2:24][CH3:25])[CH2:23][O:22][CH2:21]2)=[O:17])[CH:11]=1.C(N(CC)CC)C.O>ClCCl>[CH2:24]([C:20]12[CH2:21][O:17][C:16]([C:12]3[CH:11]=[N:10][CH:15]=[CH:14][CH:13]=3)([O:18][CH2:19]1)[O:22][CH2:23]2)[CH3:25]

Participants

6

Reactant 4

HCID 962WaterHCID 8000Boron trifluoride etherateHCID 8471TriethylamineHCID 19992002(3-Ethyloxetan-3-yl)methyl 3-pyridinecarboxylate

Product 1

HCID 199920204-Ethyl-1-(3-pyridyl)-2,6,7-trioxabicyclo[2.2.2]octane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron trifluoride etherate (1.50 ml.) was added to a stirred solution of (3-ethyl-oxetan-3-yl)methyl 3pyridinecarboxylate) (1.10 gm.) in dry dichloromethane at -70°, under a current of dry nitrogen. The stirred mixture was allowed to warm up to room temperature over a period of six hours. Triethylamine (5 ml) was added and the mixture was poured into water. The aqueous mixture was extracted with dichloromethane. The extracts were washed with water, dried over anhydrous magnesium sulphate and the solvent was removed in vacuo. The residue was purified by chromatography on alumina (Alumina Woelm TSC) eluting with 1:1 dichloromethane:hexane, saturated with ammonia. 4-Ethyl-1-(3-pyridyl)-2,6,7-trioxabicyclo[2.2.2]octane was obtained as colourless crystals (Mpt. 58°-60°, from ether, hexane).

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 alumina (Alumina Woelm TSC)
  6. washeluting with 1:1 dichloromethane

Sources & evidence

ORD record
ord-36bfde4ec6e8429e9209b303a9086810
Source dataset
uspto-grants-1991_10
Patent number
US05057504

Linked notes

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