Triphenylphosphine → Methyl 3-[4-[(3-anilinobenzyl)oxy]phenyl]propanoate

HRID 2422310

Reaction equation

HRID 2422310 reaction equation
[NH:1]([C:8]1[CH:9]=[C:10]([CH2:14][OH:15])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])=[CH:19][CH:18]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[NH:1]([C:8]1[CH:9]=[C:10]([CH:11]=[CH:12][CH:13]=1)[CH2:14][O:15][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])=[CH:19][CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 79706Benzenepropanoic acid, 4-hydroxy-, methyl esterHCID 12882229(3-(Phenylamino)phenyl)methanolHCID 66777355Diethylazodicarboxylate toluene

Product 1

HCID 57541953Methyl 3-[4-[(3-anilinobenzyl)oxy]phenyl]propanoateYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of (3-anilinophenyl)methanol (1.12 g, 5.62 mmol), methyl 3-(4-hydroxyphenyl)propanoate (1.22 g, 6.75 mmol), triphenylphosphine (1.92 g, 7.31 mmol) and tetrahydrofuran (20 mL) was added diethyl azodicarboxylate toluene solution (40%, 3.32 mL) with stirring at 0° C. and the mixture was stirred at room temperature for 14 hrs. The reaction mixture was concentrated, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-2/1) to give the title compound (1.01 g, yield 50%) as beige crystals.

Workup

  1. stirringthe mixture was stirred at room temperature for 14 hrs
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-2/1)

Sources & evidence

ORD record
ord-91d14e223e39464da398c116911a8c17
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Linked notes

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