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

HRID 984427Notes

Reaction equation

HRID 984427 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](/[CH3:12])=[CH:9]/[CH2:10][OH:11])=[CH:4][CH:3]=1.[CH2:13]([O:15][C@@H:16]([CH2:22][C:23]1[CH:28]=[CH:27][C:26](O)=[CH:25][CH:24]=1)[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH3:14]>>[CH2:13]([O:15][C@@H:16]([CH2:22][C:23]1[CH:24]=[CH:25][C:26]([O:11][CH2:10]/[CH:9]=[C:8](/[C:5]2[CH:4]=[CH:3][C:2]([I:1])=[CH:7][CH:6]=2)\[CH3:12])=[CH:27][CH:28]=1)[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH3:14]

Participants

3

Reactant 2

HCID 9816147Ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoateHCID 11437263(E)-3-(4-iodophenyl)-but-2-en-1-ol

Product 1

HCID 86589969(E)-(S)-Ethyl 2-Ethoxy-3-{4-[3-(4-Iodophenyl)-but-2-enyloxy]-phenyl}-propionateYield 80.5%

Procedure

The title compound (398 mg, 80%) was prepared as a colourless gum, from (E)-3-(4-iodophenyl)-but-2-en-1-ol (example 107a) (275 mg, 1.0 mmol) and (S)-ethyl 2-ethoxy-3-(4-hydroxyphenyl)-propionate (256 mg, 1.07 mmol) by a procedure analogous to that described in example 52c.

Sources & evidence

ORD record
ord-4dbbea7020d9482e890d246319e216cc
Source dataset
uspto-grants-2005_03
Patent number
US06867218B2

Reaction notes

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