Tributylphosphine → (E)-(2S)-3-[4-(3-Biphenyl-4-yl-3-phenyl-allyloxy)-phenyl]-2-ethoxy-propionic acid ethyl ester

HRID 488437Notes

Reaction equation

HRID 488437 reaction equation
[C:1]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:6]=[CH:5][C:4](/[C:7](/[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8]/[CH2:9][OH:10])=[CH:3][CH:2]=1.C(P(CCCC)CCCC)CCC.[CH2:36]([O:38][C:39](=[O:52])[C@@H:40]([O:49][CH2:50][CH3:51])[CH2:41][C:42]1[CH:47]=[CH:46][C:45](O)=[CH:44][CH:43]=1)[CH3:37]>C1C=CC=CC=1>[CH2:36]([O:38][C:39](=[O:52])[C@@H:40]([O:49][CH2:50][CH3:51])[CH2:41][C:42]1[CH:47]=[CH:46][C:45]([O:10][CH2:9]/[CH:8]=[C:7](/[C:4]2[CH:3]=[CH:2][C:1]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[CH:6][CH:5]=2)\[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:44][CH:43]=1)[CH3:37]

Participants

5

Reactant 3

HCID 13831TributylphosphineHCID 9816147Ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoateHCID 22270316(E)-3-biphenyl-4-yl-3-phenyl-prop-2-en-1-ol

Product 1

HCID 69774067(E)-(2S)-3-[4-(3-Biphenyl-4-yl-3-phenyl-allyloxy)-phenyl]-2-ethoxy-propionic acid ethyl esterYield 83.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Reaction of (E)-3-biphenyl-4-yl-3-phenyl-prop-2-en-1-ol (1.0 g, 3.49 mmol), tributylphosphine (1.3 ml, 5.24 mmol), (2S)-2-ethoxy-3-(4-hydroxy-phenyl)-propionic acid ethyl ester (0.92 g, 3.84 mmol) and azodicarboxylic dipiperidide (1.32 g, 5.24 mmol) in benzene in an identical manner to example 3 gave the title compound (1.47 g, 83%).

Sources & evidence

ORD record
ord-6f93cc6f1d64404598bf978928ca863b
Source dataset
uspto-grants-2005_12
Patent number
US06972294B1

Reaction notes

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