Methanol → 2-(2,5-Bis-phenylethynylphenyl)-5-(4-octyloxyphenyl)-[1,3,4]oxadiazole

HRID 458491

反応式

HRID 458491 の反応式
[O:1]1[CH:5]=[N:4][N:3]=[CH:2]1.[C:6]1([C:12]#[CH:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:14][OH:15].C(Cl)Cl.[CH3:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].CCN([CH2:30][CH3:31])CC>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[C:6]1([C:12]#[C:13][C:21]2[CH:20]=[CH:19][C:24]([C:13]#[C:12][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)=[CH:23][C:22]=2[C:5]2[O:1][C:2]([C:6]3[CH:11]=[CH:10][C:14]([O:15][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:30][CH3:31])=[CH:8][CH:7]=3)=[N:3][N:4]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

参加物

8

反応物 5

HCID 887MethanolHCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 974281,3,4-OxadiazoleHCID 21226440Methylenechloride Hexane

生成物 1

HCID 588207582-(2,5-Bis-phenylethynylphenyl)-5-(4-octyloxyphenyl)-[1,3,4]oxadiazole収率 72%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418397HCID 178418397、化合物触媒

実験手順

Pd(PPh3)4 (71.6 mg, 0.1 mmol) and CuI (23.6 mg, 0.1 mmol) were added to a mixture of 2,(2,5-dibromophenyl)-5-[4-octyloxy)phenyl]-1,3,4-oxadiazole (3.20 g, 6.3 mmol) and phenyl acetylene (1.29 g, 12.6 mmol) in 20 mL of dry Et3N. The reaction mixture was magnetically stirred for 3 h under reflux. The cooled reaction mixture was poured into an excess amount of methanol and the precipitate was collected by filtration. Re-crystallization from methylene chloride/hexane gave 2-(2,5-bis-phenylethynylphenyl)-5-(4-octyloxyphenyl)-[1,3,4]oxadiazole (2.50 g, 72% yield).

後処理

  1. temperatureunder reflux
  2. customThe cooled reaction mixture
  3. filtrationthe precipitate was collected by filtration

出典と根拠

ORDレコード
ord-340e44f6bf814d0e96218d1447b0f382
出典データセット
uspto-grants-2007_03
特許番号
US07192657B2

関連ノート

読み込み中…