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

HRID 273396

Reaction equation

HRID 273396 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-15d8bc15785e4575bd3d9f7d1597243e
Source dataset
uspto-grants-2008_11
Patent number
US07456218B2

Linked notes

Loading…