2-Methylfuran → HCID 22998481、化合物

HRID 234430

反応式

HRID 234430 の反応式
[Li]C(C)(C)C.[CH3:6][C:7]1[O:8][CH:9]=[CH:10][CH:11]=1.Br[C:13]1[S:17][C:16]([S:18]([N:21]2[CH:25]=[CH:24][CH:23]=[CH:22]2)(=[O:20])=[O:19])=[CH:15][CH:14]=1>C1COCC1.[Cl-].[Zn+2].[Cl-].[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:6][C:7]1[O:8][C:9]([C:13]2[S:17][C:16]([S:18]([N:21]3[CH:25]=[CH:24][CH:23]=[CH:22]3)(=[O:19])=[O:20])=[CH:15][CH:14]=2)=[CH:10][CH:11]=1

参加物

7

反応物 3

HCID 107972-MethylfuranHCID 23445587N-(5-bromothiophenesulfonyl)pyrroleHCID 178418306HCID 178418306、化合物

生成物 1

HCID 22998481HCID 22998481、化合物収率 19.3%

試薬・触媒・溶媒 3

HCID 3007855Zincchloride触媒HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
-10 °C

実験手順

t-BuLi (1.7 m solution in hexane, 7.9 ml, 14.6 mmol) was added dropwise under constant stirring under a nitrogen atmosphere to a solution of 2-methylfuran (1.0 g, 12 mmol) in THF (20 ml) at -78° C. The solution was then warmed to -10° C. and stirring continued for 45 min. The solution was then added to a solution of zinc chloride (27 ml of a 0.5M solution in THF) at -30° C. and then warmed to room temperature where stirring continued for 1 hr. resulting in a pale yellow clear solution. The solution was then transferred via a steel canula under nitrogen to a solution of N-(5-bromothiophene-2-sulfonyl)pyrrole (Example 33A, 3.5 g, 12 mmol) and tetrakis(triphenylphosphine)-palladium (0) (693 mg, 0.6 mmol) in THF (15 ml) at -78° C. The solution was then warmed to room temperature and stirred for a period of 2 hours. Purification by column chromatography using 2% ethyl acetate gave 680 mg of N-[5-(2-methyl-5-furyl)thiophene-2-sulfonyl]pyrrole as a pale yellow powder (19% yield).

後処理

  1. temperaturewarmed to room temperature where
  2. stirringstirring
  3. waitcontinued for 1 hr
  4. customresulting in a pale yellow clear solution
  5. temperatureThe solution was then warmed to room temperature
  6. stirringstirred for a period of 2 hours
  7. customPurification by column chromatography

出典と根拠

ORDレコード
ord-bcaac69dab8048f9bc83dbb0247428f4
出典データセット
uspto-grants-1997_01
特許番号
US05594021

関連ノート

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