Acetonitrile → 6-(5-Fluoro-2-methylphenyl)-1-(3-fluoro-2-nitrophenyl)-6-methyl-4-trifluoromethylhept-1-yn-4-ol

HRID 400663ノート

反応式

HRID 400663 の反応式
[F:1][C:2]1[C:3]([N+:16]([O-:18])=[O:17])=[C:4](OS(C(F)(F)F)(=O)=O)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.C(#N)C.[F:29][C:30]1[CH:31]=[CH:32][C:33]([CH3:49])=[C:34]([C:36]([CH3:48])([CH3:47])[CH2:37][C:38]([C:43]([F:46])([F:45])[F:44])([OH:42])[CH2:39][C:40]#[CH:41])[CH:35]=1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I.O1CCCC1>[F:29][C:30]1[CH:31]=[CH:32][C:33]([CH3:49])=[C:34]([C:36]([CH3:47])([CH3:48])[CH2:37][C:38]([C:43]([F:44])([F:45])[F:46])([OH:42])[CH2:39][C:40]#[C:41][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=2[N+:16]([O-:18])=[O:17])[CH:35]=1

参加物

9

反応物 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 469390162-(1,1-Dimethyl-3-hydroxy-3-trifluoromethyl-5-hexynyl)-4-fluorotolueneHCID 600266203-Fluoro-2-nitrophenyl trifluoromethanesulphonate

生成物 1

HCID 600264926-(5-Fluoro-2-methylphenyl)-1-(3-fluoro-2-nitrophenyl)-6-methyl-4-trifluoromethylhept-1-yn-4-ol収率 45.3%

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 67553Tetrabutylammonium Iodide触媒HCID 178418476HCID 178418476、化合物触媒HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of trifluoromethanesulfonic acid 3-fluoro-2-nitrophenyl ester (149 mg, 0.52 mmol), dichlorobis(triphenylphosphine)palladium (II) (20 mg, 0.028 mmol), copper (I) iodide (14 mg, 0.074 mmol), tetrabutyl ammonium iodide (200 mg, 0.54 mmol), 0.25 mL of anhydrous triethylamine, 0.5 mL of anhydrous acetonitrile, and 0.5 mL of anhydrous tetrahydrofuran was stirred at room temperature for 30 minutes. The resulting mixture was treated with 6-(5-fluoro-2-methylphenyl)-6-methyl-4-trifluoromethylhept-1-yn-4-ol (145 mg, 0.48 mmol) and stirred at room temperature for 18 hours. The crude product was purified by chromatography on SiO2 (50% hexanes in dichloromethane) to give 96 mg of the title product as light yellow oil, (45% yield).

後処理

  1. stirringstirred at room temperature for 18 hours
  2. customThe crude product was purified by chromatography on SiO2 (50% hexanes in dichloromethane)

出典と根拠

ORDレコード
ord-e66f46184a51474db2757ffd1848176d
出典データセット
uspto-grants-2014_06
特許番号
US08741897B2

反応ノート

読み込み中…