Triphenylphosphine → HCID 23121721, compound

HRID 1631190Notes

Reaction equation

HRID 1631190 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[C:14]1([CH2:20][CH2:21][CH2:22]O)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[C:14]1([CH2:20][CH2:21][CH2:22][O:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:7]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 31234BenzenepropanolHCID 79706Benzenepropanoic acid, 4-hydroxy-, methyl esterHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 23121721HCID 23121721, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-(4-hydroxyphenyl)propanoate (2.50 g) and 3-phenylpropan-1-ol (2.8 mL) in tetrahydrofuran (70 mL), triphenylphosphine (5.46 g) was added at room temperature. Next, diethyl azodicarboxylate (9.4 mL, 40% toluene solution) was added dropwise thereto, followed by stirring at room temperature for 2 hours. Then, the reaction mixture was concentrated and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1 to 5:1) to give the title compound (3.02 g) having the following physical properties.

Workup

  1. concentrationThen, the reaction mixture was concentrated
  2. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1 to 5:1)

Sources & evidence

ORD record
ord-be3d1be1352b49308a54e961660ac9af
Source dataset
uspto-grants-2014_07
Patent number
US08791159B2

Reaction notes

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