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Triphenylphosphine → 3-(3-Quinuclidinyloxy)isoxazole

HRID 263454
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HRID 263454 반응식
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[OH:32][C:33]1[CH:37]=[CH:36][O:35][N:34]=1.O[CH:39]1[CH:44]2[CH2:45][CH2:46][N:41]([CH2:42][CH2:43]2)[CH2:40]1>O1CCCC1>[N:41]12[CH2:46][CH2:45][CH:44]([CH2:43][CH2:42]1)[CH:39]([O:32][C:33]1[CH:37]=[CH:36][O:35][N:34]=1)[CH2:40]2
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참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 15381(+-)-3-QuinuclidinolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 178516613HCID 178516613, 화합물

생성물 1

HCID 101980493-(3-Quinuclidinyloxy)isoxazole수율 76.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran
용매

실험 절차

A solution of 9.18 g of triphenylphosphine in 100 ml of tetrahydrofuran was cooled to 5° C. 6.10 g of diethyl azodicarboxylate were then added dropwise to the cooled solution, after which 2.98 g of 3-hydroxyisoxazole and 4.45 g of 3-hydroxyquinuclidine were added, and the resulting mixture was stirred at room temperature for 24 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel, using ethyl acetate as the eluent, to afford 5.18 g (yield 76.2%) of the title compound as a colorless powder, melting at 80°-81° C.

후처리

  1. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  2. customthe resulting residue was purified by column chromatography through silica gel

출처 및 근거

ORD 기록
ord-45a5c665ce2f43eeabe63b686c57eea9
출처 데이터셋
uspto-grants-1997_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05643923

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