Triphenylphosphine → HCID 23159903, compound

HRID 2110899Notes

Reaction equation

HRID 2110899 reaction equation
[CH3:1][C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][OH:15])=[CH:10][CH:9]=2)[N:5]=[C:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:3]=1.O[C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][C:31]([O:33][CH3:34])=[O:32])=[CH:25][CH:24]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>ClCCl>[CH3:1][C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][O:15][C:23]3[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][C:31]([O:33][CH3:34])=[O:32])=[CH:25][CH:24]=3)=[CH:10][CH:9]=2)[N:5]=[C:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:3]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 79706Benzenepropanoic acid, 4-hydroxy-, methyl esterHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 23159933HCID 23159933, compound

Product 1

HCID 23159903HCID 23159903, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of {4-[(5-methyl-3-phenyl-1H-pyrazol-1-yl)methyl]phenyl}methanol (278 mg, 1.0 mmol), methyl 3-(4-hydroxyphenyl)propanoate (180 mg, 1.0 mmol), triphenylphosphine (393 mg, 1.5 mmol) and dichloromethane (5 mL) was added dropwise diethyl azodicarboxylate (40% toluene solution, 650 mg, 1.5 mmol) with stirring at room temperature, and the mixture was stirred at room temperature for 1 hr. After completion of the reaction, the reaction mixture was purified by silica gel column chromatography (hexane:ethyl acetate=19:1-1:2) to give the title compound (263 mg, yield 90%) as a yellow oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hr
  2. customAfter completion of the reaction
  3. customthe reaction mixture was purified by silica gel column chromatography (hexane:ethyl acetate=19:1-1:2)

Sources & evidence

ORD record
ord-2a4cd38232b34b6cba8f79964b8805aa
Source dataset
uspto-grants-2009_04
Patent number
US07517910B2

Reaction notes

Loading…