Tributylphosphine → HCID 69773863, compound

HRID 488451Notes

Reaction equation

HRID 488451 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.C(P(CCCC)CCCC)CCC.[CH2:31]([O:33][C:34](=[O:47])[C@@H:35]([O:44][CH2:45][CH3:46])[CH2:36][C:37]1[CH:42]=[CH:41][C:40](O)=[CH:39][CH:38]=1)[CH3:32]>C1C=CC=CC=1>[CH2:31]([O:33][C:34](=[O:47])[C@@H:35]([O:44][CH2:45][CH3:46])[CH2:36][C:37]1[CH:42]=[CH:41][C:40]([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:39][CH:38]=1)[CH3:32]

Participants

5

Reactant 3

HCID 13831TributylphosphineHCID 9816147Ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoateHCID 67146538HCID 67146538, compound

Product 1

HCID 69773863HCID 69773863, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Reaction of (E)-3-(4-bromophenyl)-3-phenyl-prop-2-en-1-ol (289 mg, 1.0 mmol), tributylphosphine (0.37 ml, 1.5 mmol), (2S)-2-ethoxy-3-(4-hydroxy-phenyl)-propionic acid ethyl ester (262 mg, 1.10 mmol) and azodicarboxylic dipiperidide (378 mg, 1.5 mmol) in benzene in an identical manner to example 3 gave the title compound (460 mg, 90%).

Sources & evidence

ORD record
ord-e932d0a6369448a4a60c3ce6ad6168f9
Source dataset
uspto-grants-2005_12
Patent number
US06972294B1

Reaction notes

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