Triphenylphosphine → 5-[2-(2,6-Dimethyl-4'-trifluoromethyl-biphenyl-4-yloxy)-1,1-dimethyl-ethyl]-thiophene-2-carboxylic acid methyl ester

HRID 660986ノート

反応式

HRID 660986 の反応式
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:10]([CH3:14])([CH3:13])[CH2:11][OH:12])=[CH:8][CH:9]=1)=[O:4].[CH3:15][C:16]1[CH:21]=[C:20](O)[CH:19]=[C:18]([CH3:23])[C:17]=1[C:24]1[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1(C)C=CC=CC=1.CO>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:10]([CH3:14])([CH3:13])[CH2:11][O:12][C:20]2[CH:21]=[C:16]([CH3:15])[C:17]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:31])([F:33])[F:32])=[CH:26][CH:25]=3)=[C:18]([CH3:23])[CH:19]=2)=[CH:8][CH:9]=1)=[O:4]

参加物

7

反応物 4

HCID 11776TriphenylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 569717492,6-Dimethyl-4'-(trifluoromethyl)-[1,1'-biphenyl]-4-olHCID 67484466Methyl 5-(1-hydroxy-2-methylpropan-2-yl)thiophene-2-carboxylate

生成物 1

HCID 593559295-[2-(2,6-Dimethyl-4'-trifluoromethyl-biphenyl-4-yloxy)-1,1-dimethyl-ethyl]-thiophene-2-carboxylic acid methyl ester収率 42%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

A mixture of 5-(2-hydroxy-1,1-dimethyl-ethyl)-thiophene-2-carboxylic acid methyl ester (0.436 g, 2.04 mmol), 2,6-dimethyl-4′-trifluoromethyl-biphenyl-4-ol (0.596 g, 2.24 mmol), and PPh3 (0.793 g, 3.02 mmol) is dissolved in toluene (20 mL), treated with 1,1′-(azodicarbonyl)dipiperidine (ADDP, 0.763 g, 3.02 mmol), and stirred overnight at 80° C. The mixture is then cooled to rt, diluted with MeOH until homogeneous, and concentrated. The residue is loaded onto silica gel and eluted using hexanes with an ethyl acetate gradient from 0% to 40% to afford 5-[2-(2,6-dimethyl-4′-trifluoromethyl-biphenyl-4-yloxy)-1,1-dimethyl-ethyl]-thiophene-2-carboxylic acid methyl ester (0.394 g, 42%). MS (ES): 463.3 [M+H]+.

後処理

  1. temperatureThe mixture is then cooled to rt
  2. concentrationconcentrated
  3. washeluted

出典と根拠

ORDレコード
ord-996cda2a683641c991574375c43bd1dd
出典データセット
uspto-grants-2011_12
特許番号
US08084489B2

反応ノート

読み込み中…