Triphenylphosphine → HCID 69797104, compound

HRID 984307Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11](/[C:14](/[CH3:18])=[CH:15]/[CH2:16][OH:17])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[CH2:50]([O:52][C@@H:53]([CH2:59][C:60]1[CH:65]=[CH:64][C:63](O)=[CH:62][CH:61]=1)[C:54]([O:56][CH2:57][CH3:58])=[O:55])[CH3:51]>>[CH2:57]([O:56][C:54](=[O:55])[C@@H:53]([O:52][CH2:50][CH3:51])[CH2:59][C:60]1[CH:65]=[CH:64][C:63]([O:17][CH2:16]/[CH:15]=[C:14](/[C:11]2[CH:12]=[CH:13][C:8]([C:5]3[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=3)=[CH:9][CH:10]=2)\[CH3:18])=[CH:62][CH:61]=1)[CH3:58]

Participants

Reactant 4

HCID 11776Triphenylphosphine

HCID 220568ethyl N-ethoxycarbonyliminocarbamate

HCID 9816147Ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoate

HCID 69796253HCID 69796253, compound

Product 1

HCID 69797104HCID 69797104, compoundYield 34.4%

Procedure

The title compound was prepared from (E)-3-(4′-bromo-biphenyl-4-yl)-but-2-en-1-ol (0.364 g, 1.2 mmol), triphenylphosphine (0.328 g, 1.3 mmol), diethyl azodicarboxylate (0.173 ml, 1.1 mmol) and (S)-ethyl 2-ethoxy-3-(4-hydroxy-phenyl)-propionate (0.238 g, 1.0 mmol) by a procedure analogous to that described in example 1c, yielding 0.180 g (34%) of (E)-(S)-3-{4-[3-(4′-bromo-biphenyl-4-yl)-but-2-enyloxy]-phenyl}-2-ethoxy-propionic acid ethyl ester.

Sources & evidence

ORD record: ord-d0091f0e3fa64d0c8653a6cc2a7e866e
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06867218B2

Reaction notes

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