Triphenylphosphine → HCID 57541958, compound

HRID 2422279Notes

Reaction equation

HRID 2422279 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.[CH3:14][C:15]1[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[C:16]=1[CH2:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH2:21]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1(C)C=CC=CC=1>[CH3:14][C:15]1[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[C:16]=1[CH2:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH2:21][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 79706Benzenepropanoic acid, 4-hydroxy-, methyl esterHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 23083075HCID 23083075, compound

Product 1

HCID 57541958HCID 57541958, compoundYield 32.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of methyl 3-(4-hydroxyphenyl)propanoate (180 mg), 3-(2,6-dimethylbenzyl)benzyl alcohol (226 mg) and triphenylphosphine (286 mg) in toluene (2 mL) was added dropwise diethyl azodicarboxylate (40% toluene solution 500 mg) at room temperature, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was purified by silica gel column chromatography with ethyl acetate-hexane (gradient of 1:9 to 3:2 by volume ratio) to give the title compound (125 mg, yield 32%) as a pale-yellow oil.

Workup

  1. customThe reaction mixture was purified by silica gel column chromatography with ethyl acetate-hexane (gradient of 1:9 to 3:2 by volume ratio)

Sources & evidence

ORD record
ord-15801882be074699a979da77dc6e40a2
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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