Triphenylphosphine → HCID 68859199, compound

HRID 493515Notes

Reaction equation

HRID 493515 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH3:17][O:18][C:19](=[O:29])[CH:20](O)[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C(OCC)C>[CH3:17][O:18][C:19](=[O:29])[CH:20]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1)[CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 1380784-Hydroxy-4'-nitrobiphenylHCID 518800Methyl 2-hydroxy-3-phenylpropanoate

Product 1

HCID 68859199HCID 68859199, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 4′-hydroxy-4-nitro-biphenyl (4.12 g, 19.1 mmol), prepared in step 2 of Example 16, 2-hydroxy-3-phenyl-propionic acid methyl ester (3.35 g, 18.5 mmol) and triphenylphosphine (4.12 g, 19.1 mmol) in diethyl ether was cooled under nitrogen to 0° C. Diisopropyl azodicarboxylate (6.09 mL, 30.96 mmol) was then added and the reaction allowed to come to room temperature and then stirred overnight at room temperature. The reaction was concentrated under reduced pressure. Purification of the residue on silica gel using 15% ethyl acetate hexanes as the eluent gave 2-(4′-nitro-biphenyl-4-yloxy)-3-phenyl-propionic acid methyl ester.

Workup

  1. customto come to room temperature
  2. concentrationThe reaction was concentrated under reduced pressure
  3. customPurification of the residue on silica gel using 15% ethyl acetate hexanes as the eluent

Sources & evidence

ORD record
ord-52faffd86cf34fc8b3a6bc8695541e6c
Source dataset
uspto-grants-2009_05
Patent number
US07534894B2

Reaction notes

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