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

HRID 488449Notes

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.C(P(CCCC)CCCC)CCC.[CH2:32]([O:34][C:35](=[O:48])[C@@H:36]([O:45][CH2:46][CH3:47])[CH2:37][C:38]1[CH:43]=[CH:42][C:41](O)=[CH:40][CH:39]=1)[CH3:33]>>[CH2:32]([O:34][C:35](=[O:48])[C@@H:36]([O:45][CH2:46][CH3:47])[CH2:37][C:38]1[CH:43]=[CH:42][C:41]([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:40][CH:39]=1)[CH3:33]

Participants

Reactant 3

HCID 13831Tributylphosphine

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

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

Product 1

HCID 69774070(2S)-3-{4-[3,3-Bis-(4-bromophenyl)-allyloxy]-phenyl}-2-ethoxy-propionic acid ethyl esterYield 75.5%

Procedure

Reaction of 3,3-bis-(4-bromophenyl)-prop-2-en-1-ol (2.60 g, 7.0 mmol), tributylphosphine (2.52 g, 10.0 mmol), (2S)-2-ethoxy-3-(4-hydroxy-phenyl)-propionic acid ethyl ester (1.50 g, 6.3 mmol) and azodicarboxylic dipiperidide (2.02 g, 10.0 mmol) in an identical manner to example 3 gave the title compound (2.8 g, 75%).

Sources & evidence

ORD record: ord-8c85ffe9d1184af58458a690469d57ed
Source dataset: uspto-grants-2005_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06972294B1

Reaction notes

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