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

HRID 661000

반응식

HRID 661000 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].[C:14]([C:18]1[CH:23]=[CH:22][C:21]([C:24]2[C:29]([CH3:30])=[CH:28][C:27](O)=[CH:26][C:25]=2[CH3:32])=[CH:20][CH:19]=1)([CH3:17])([CH3:16])[CH3:15].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:27]2[CH:28]=[C:29]([CH3:30])[C:24]([C:21]3[CH:22]=[CH:23][C:18]([C:14]([CH3:16])([CH3:15])[CH3:17])=[CH:19][CH:20]=3)=[C:25]([CH3:32])[CH:26]=2)[CH3:12])=[CH:9][CH:10]=1)=[O:5])[CH3:2]

참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 533020184'-Tert-butyl-2,6-dimethylbiphenyl-4-OLHCID 59355961Ethyl 5-(1-hydroxyethyl)thiophene-2-carboxylate

생성물 1

HCID 67484337(+/-)-5-[1-(4'-Tert-butyl-2,6-dimethyl-biphenyl-4-yloxy)-ethyl]-thiophene-2-carboxylic acid ethyl ester수율 671%

시약·촉매·용매 2

HCID 887Methanol용매HCID 1140Toluene용매

실험 절차

A mixture of (±)-5-(1-hydroxy-ethyl)-thiophene-2-carboxylic acid ethyl ester (0.416 g, 2.08 mmol), 4′-tert-butyl-2,6-dimethyl-biphenyl-4-ol (0.561 g, 2.20 mmol), and PPh3 (0.787 g, 3.00 mmol) is dissolved in toluene (19 mL) and treated with 1,1′-(azodicarbonyl)dipiperidine (ADDP, 0.760 g, 3.01 mmol) and stirred overnight at rt. The mixture is diluted with MeOH until homogeneous and conc. The residue is loaded onto silica gel and eluted using hexanes with an ethyl acetate gradient from 0% to 40% giving (±)-5-[1-(4′-tert-butyl-2,6-dimethyl-biphenyl-4-yloxy)-ethyl]-thiophene-2-carboxylic acid ethyl ester (0.604 g, 671%) as a clear syrup.

후처리

  1. washeluted

출처 및 근거

ORD 기록
ord-1cf785b3ae694482950d6fcc298a9d3d
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084489B2

연결된 노트

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