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

HRID 583130ノート

反応式

HRID 583130 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3c6d65742bde44c29fc788d45208a8ad
出典データセット
uspto-grants-1999_07
特許番号
US05929089

反応ノート

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