Triphenylphosphine → Ethyl 3-(4-benzyloxyphenyl)-2-(4-cyanophenoxy)propionate

HRID 1860079Notes

Reaction equation

HRID 1860079 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([OH:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]([C:25]1[CH:30]=[CH:29][C:28](O)=[CH:27][CH:26]=1)#[N:24].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([O:22][C:28]2[CH:29]=[CH:30][C:25]([C:23]#[N:24])=[CH:26][CH:27]=2)[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 130194-CyanophenolHCID 5462977Diethyl azodicarboxylateHCID 151861533-(4-Benzyloxyphenyl)-2-hydroxypropionic acid ethyl ester

Product 1

HCID 18626028Ethyl 3-(4-benzyloxyphenyl)-2-(4-cyanophenoxy)propionateYield 45.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a similar manner to that described in Example 122, a reaction was carried out using ethyl 3-(4-benzyloxyphenyl)lactate (1.01 g), which is the product of Reference example 1(b), 4-cyanophenol (481 mg), triphenylphosphine (1.06 g) and solution of diethylazodicarboxylate in toluene (40%, 0.73 ml) and the reaction mixture was treated to afford the desired compound (619 mg) as a colorless oil.

Workup

  1. additionthe reaction mixture was treated

Sources & evidence

ORD record
ord-330576b2d44f4fc2b1319f5c90a94ab0
Source dataset
uspto-grants-2003_03
Patent number
US06528525B1

Reaction notes

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