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

HRID 660981ノート

反応式

HRID 660981 の反応式
[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]([CH:11]([OH:13])[CH3:12])=[CH:9][CH:10]=1)=[O:5])[CH3:2].[CH3:14][C:15]1[CH:20]=[C:19](O)[CH:18]=[C:17]([CH3:22])[C:16]=1[C:23]1[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=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>[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]([CH:11]([O:13][C:19]2[CH:20]=[C:15]([CH3:14])[C:16]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([F:30])([F:32])[F:31])=[CH:25][CH:24]=3)=[C:17]([CH3:22])[CH:18]=2)[CH3:12])=[CH:9][CH:10]=1)=[O:5])[CH3:2]

参加物

7

反応物 4

HCID 11776TriphenylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 569717492,6-Dimethyl-4'-(trifluoromethyl)-[1,1'-biphenyl]-4-olHCID 59355961Ethyl 5-(1-hydroxyethyl)thiophene-2-carboxylate

生成物 1

HCID 67485105(+/-)-5-[1-(2,6-Dimethyl-4'-trifluoromethyl-biphenyl-4-yloxy)-ethyl]-thiophene-2-carboxylic acid ethyl ester収率 71%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 1140Toluene溶媒

実験手順

A mixture of (±)-5-(1-hydroxy-ethyl)-thiophene-2-carboxylic acid ethyl ester (0.402 g, 2.01 mmol), 2,6-dimethyl-4′-trifluoromethyl-biphenyl-4-ol (0.593 g, 2.23 mmol), and PPh3 (0.798 g, 3.04 mmol) is dissolved in toluene (20 mL) and treated with 1,1′-(azodicarbonyl)dipiperidine (ADDP, 0.763 g, 3.02 mmol) and stirred overnight at rt. The mixture is 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% giving (±)-5-[1-(2,6-Dimethyl-4′-trifluoromethyl-biphenyl-4-yloxy)-ethyl]-thiophene-2-carboxylic acid ethyl ester (0.638 g, 71%) as a clear syrup. MS (ES): 447.3 [M−H]−.

後処理

  1. concentrationconcentrated
  2. washeluted

出典と根拠

ORDレコード
ord-b65ea3a333374b1db8e8b4502ea79785
出典データセット
uspto-grants-2011_12
特許番号
US08084489B2

反応ノート

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