Triphenylphosphine → 3-{4-[3,3-Bis-(4-bromo-phenyl)-allyloxy]-phenyl}-2-ethoxy-propionic acid ethyl ester

HRID 488439Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=2)=[CH:9][CH2:10][OH:11])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:38]([O:40][C:41](=[O:54])[CH:42]([O:51][CH2:52][CH3:53])[CH2:43][C:44]1[CH:49]=[CH:48][C:47](O)=[CH:46][CH:45]=1)[CH3:39].CCOC(/N=N/C(OCC)=O)=O>>[CH2:38]([O:40][C:41](=[O:54])[CH:42]([O:51][CH2:52][CH3:53])[CH2:43][C:44]1[CH:49]=[CH:48][C:47]([O:11][CH2:10][CH:9]=[C:8]([C:12]2[CH:13]=[CH:14][C:15]([Br:18])=[CH:16][CH:17]=2)[C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=2)=[CH:46][CH:45]=1)[CH3:39]

Participants

Reactant 4

HCID 11776Triphenylphosphine

HCID 5462977Diethyl azodicarboxylate

HCID 11791243Ethyl 2-ethoxy-3-(4-hydroxyphenyl)propanoate

HCID 222703043,3-Bis-(4-bromophenyl)prop-2-en-1-ol

Product 1

HCID 541884073-{4-[3,3-Bis-(4-bromo-phenyl)-allyloxy]-phenyl}-2-ethoxy-propionic acid ethyl esterYield 56.2%

Procedure

Reaction of 3,3-bis-(4-bromophenyl)-prop-2-en-1-ol (0.50 g, 1.36 mmol), triphenylphosphine (0.39 g, 1.50 mmol), 2-ethoxy-3-(4-hydroxy-phenyl)-propionic acid ethyl ester (0.39 g, 1.63 mmol) and diethy lazodicarboxylate (0.26 g, 1.51 mmol) in an identical manner to example 1 gave the title compound (450 mg, 56%).

Sources & evidence

ORD record: ord-cba61c894ff44918856441ff78a8a1b9
Source dataset: uspto-grants-2005_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06972294B1

Reaction notes

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