Ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoate → (E)-(S)-Ethyl 2-Ethoxy-3-{4-[3-(4'-fluoro-biphenyl-4-yl)-but-2-enyloxy]-phenyl}-propionate

HRID 984425Notes

Reaction equation

HRID 984425 reaction equation
[F: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.[CH2:19]([O:21][C@@H:22]([CH2:28][C:29]1[CH:34]=[CH:33][C:32](O)=[CH:31][CH:30]=1)[C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH3:20]>>[CH2:19]([O:21][C@@H:22]([CH2:28][C:29]1[CH:30]=[CH:31][C:32]([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]([F:1])=[CH:7][CH:6]=3)=[CH:9][CH:10]=2)\[CH3:18])=[CH:33][CH:34]=1)[C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH3:20]

Participants

3

Reactant 2

HCID 9816147Ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoateHCID 58816048(E)-3-(4'-fluoro-biphenyl-4-yl)-but-2-en-1-ol

Product 1

HCID 86589968(E)-(S)-Ethyl 2-Ethoxy-3-{4-[3-(4'-fluoro-biphenyl-4-yl)-but-2-enyloxy]-phenyl}-propionateYield 89.1%

Procedure

The title compound (849 mg, 89%) was prepared as a colourless gum from (E)-3-(4′-fluorobiphenyl-4-yl)-but-2-en-1-ol (500 mg, 2.06 mmol) and (S)-ethyl 2-ethoxy-3-(4-hydroxyphenyl)-propionate (516 mg, 2.17 mmol) by a procedure analogous to that described in example 52c.

Sources & evidence

ORD record
ord-59c8e491c4da48db9532fd5e5632861e
Source dataset
uspto-grants-2005_03
Patent number
US06867218B2

Reaction notes

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