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

HRID 660981노트

반응식

HRID 660981 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 1140Toluene용매

실험 절차

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]−.

후처리

  1. concentrationconcentrated
  2. washeluted

출처 및 근거

ORD 기록
ord-b65ea3a333374b1db8e8b4502ea79785
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084489B2

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