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

HRID 345289

반응식

HRID 345289 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-36bfde4ec6e8429e9209b303a9086810
출처 데이터셋
uspto-grants-1991_10
특허 번호
US05057504

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