1H-1,2,4-Triazole → 1-[4-(4-Benzyloxyphenyl)butyl]-1,2,4-triazole

HRID 322253ノート

反応式

HRID 322253 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH2:18]O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(P(CCCC)CCCC)CCC.[NH:33]1[CH:37]=[N:36][CH:35]=[N:34]1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][N:33]2[CH:37]=[N:36][CH:35]=[N:34]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 92571H-1,2,4-TriazoleHCID 13831TributylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 153287654-(Phenylmethoxy)benzenebutanol

生成物 1

HCID 220098341-[4-(4-Benzyloxyphenyl)butyl]-1,2,4-triazole収率 83%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 4-(4-benzyloxyphenyl)butanol (3.55 g), tributyl phosphine (6.84 g) and 1,2,4-triazole (1.86 g) in tetrahydrofuran (75 ml) was added dropwise, at room temperature, diethyl azodicarboxylate (40% toluene solution, 11.8 g). The mixture was heated for two hours under reflux. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography. From the fraction eluted with ethyl acetate-hexane (1:2, v/v), 1-[4-(4-benzyloxyphenyl)butyl]-1,2,4-triazole (3.45 g, 83%) was obtained. Recrystallization from isopropyl ether gave colorless prisms, mp 68-69° C.

後処理

  1. temperatureThe mixture was heated for two hours
  2. temperatureunder reflux
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. washFrom the fraction eluted with ethyl acetate-hexane (1:2

出典と根拠

ORDレコード
ord-1a0c19a7a4b64cb88b3dfd22f4d5a8c4
出典データセット
uspto-grants-2001_04
特許番号
US06211215B1

反応ノート

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