Triphenylphosphine → HCID 69773860, compound

HRID 488447Notes

Reaction equation

HRID 488447 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[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.[CH2:37]([O:39][C:40](=[O:53])[C@@H:41]([O:50][CH2:51][CH3:52])[CH2:42][C:43]1[CH:48]=[CH:47][C:46](O)=[CH:45][CH:44]=1)[CH3:38].N(C(OCC)=O)=NC(OCC)=O>>[CH2:37]([O:39][C:40](=[O:53])[C@@H:41]([O:50][CH2:51][CH3:52])[CH2:42][C:43]1[CH:48]=[CH:47][C:46]([O:11][CH2:10]/[CH:9]=[C:8](\[C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=2)/[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:45][CH:44]=1)[CH3:38]

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 9816147Ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoateHCID 54476890HCID 54476890, compound

Product 1

HCID 69773860HCID 69773860, compoundYield 43.2%

Procedure

Reaction of 3-(4-bromophenyl)-3-phenyl-prop-2-en-1-ol (145 mg, 0.50 mmol), triphenylphosphine (144 mg, 0.55 mmol), (2S)-2-ethoxy-3-(4-hydroxy-phenyl)-propionic acid ethyl ester (119 mg, 0.50 mmol) and diethyl azodicarboxylate (96 mg, 0.55 mmol) in an identical manner to example 1 gave the title compound (110 mg, 43%).

Sources & evidence

ORD record
ord-6e62cdfed75c4d8d853bb062f8845c07
Source dataset
uspto-grants-2005_12
Patent number
US06972294B1

Reaction notes

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