Triphenylphosphine → 5-(5-Chloro-2,3-dihydrobenzofuran-7-yl)-3-(1-butylpiperidin-4-yl)-1,3,4-oxadiazol-2(3H)-one

HRID 583130노트

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HRID 583130 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:11]2[O:15][C:14](=[O:16])[NH:13][N:12]=2)[C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=1.[CH2:17]([N:21]1[CH2:26][CH2:25][CH:24](O)[CH2:23][CH2:22]1)[CH2:18][CH2:19][CH3:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC([O-])=O>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:11]2[O:15][C:14](=[O:16])[N:13]([CH:24]3[CH2:25][CH2:26][N:21]([CH2:17][CH2:18][CH2:19][CH3:20])[CH2:22][CH2:23]3)[N:12]=2)[C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 136652701-Butylpiperidin-4-olHCID 211877245-(5-chloro-2,3-dihydrobenzofuran-7-yl)-1,3,4-oxadiazol-2(3H)-oneHCID 86599450N-ethoxycarbonyliminocarbamate

생성물 1

HCID 213106155-(5-Chloro-2,3-dihydrobenzofuran-7-yl)-3-(1-butylpiperidin-4-yl)-1,3,4-oxadiazol-2(3H)-one수율 79.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

2.38 g (0.01 mol) of 5-(5-chloro-2,3-dihydrobenzofuran-7-yl)-1,3,4-oxadiazol-2(3H)-one, in suspension in 80 ml of tetrahydrofuran, are introduced into a 250 ml three-necked round-bottomed flask, cooled to 0° C. and placed under magnetic stirring, 1.57 g (0.01 mol) of 1-butylpiperidin-4-ol, 3.41 g (0.013 mol) of triphenylphosphine and then 2.44 g (0.014 mol) of ethyl azodicarboxylate are added and the mixture is stirred at room temperature for 3 h and then at 40° C. for 3 h. The solvent is evaporated under reduced pressure and the residue is taken up in water and extracted five times with diethyl ether. The organic phase is dried over magnesium sulphate and filtered, the solvent is evaporated under reduced pressure and the residue is purified by chromatography on a column of silica gel, elution being carried out with an 80/20 mixture of ethyl acetate and heptane. 3 g of compound are obtained. Melting point: 133.8-134° C.

후처리

  1. waitat 40° C. for 3 h
  2. customThe solvent is evaporated under reduced pressure
  3. extractionextracted five times with diethyl ether
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. filtrationfiltered
  6. customthe solvent is evaporated under reduced pressure
  7. customthe residue is purified by chromatography on a column of silica gel, elution
  8. additionbeing carried out with an 80/20 mixture of ethyl acetate and heptane

출처 및 근거

ORD 기록
ord-3c6d65742bde44c29fc788d45208a8ad
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05929089

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