Triphenylphosphine → Methyl 3-(4-{[2'-methyl-4'-(3-(pyridin-2-yl)propoxy)biphenyl-3-yl]methoxy}phenyl)propanoate

HRID 273396

反応式

HRID 273396 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][O:15][C:16]3[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])=[CH:18][CH:17]=3)[CH:9]=2)=[C:4]([CH3:28])[CH:3]=1.[N:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH2:35][CH2:36][CH2:37]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH3:28][C:4]1[CH:3]=[C:2]([O:1][CH2:37][CH2:36][CH2:35][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][N:29]=2)[CH:7]=[CH:6][C:5]=1[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])=[CH:18][CH:17]=2)[CH:9]=1

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 72922PyripropanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 58903183Methyl 3-{4-[(4'-hydroxy-2'-methylbiphenyl-3-yl)methoxy]phenyl}propanoate

生成物 1

HCID 58903135Methyl 3-(4-{[2'-methyl-4'-(3-(pyridin-2-yl)propoxy)biphenyl-3-yl]methoxy}phenyl)propanoate収率 56.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of methyl 3-{4-[(4′-hydroxy-2′-methylbiphenyl-3-yl)methoxy]phenyl}propanoate (0.602 g, 1.60 mmol), 3-(pyridin-2-yl)propan-1-ol (0.822 g, 6.00 mmol) and triphenylphosphine (1.57 g, 6.00 mmol) in tetrahydrofuran (20 mL) under ice-cooling was stirred and diethyl azodicarboxylate (40% toluene solution, 2.72 mL, 6.00 mmol) was added. The mixture was warmed to room temperature and stirred for 42 hrs. The reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (20%-60% ethyl acetate/hexane) and preparative HPLC to give the title compound as a yellow viscous oil (0.446 g, yield 56%).

後処理

  1. stirringstirred for 42 hrs
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (20%-60% ethyl acetate/hexane) and preparative HPLC

出典と根拠

ORDレコード
ord-15d8bc15785e4575bd3d9f7d1597243e
出典データセット
uspto-grants-2008_11
特許番号
US07456218B2

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