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

HRID 1268296Notes

Reaction equation

HRID 1268296 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9](/[C:12](/[CH3:16])=[CH:13]/[CH2:14][OH:15])=[CH:8][CH:7]=1.[CH2:17]([O:19][C@@H:20]([CH2:26][C:27]1[CH:32]=[CH:31][C:30](O)=[CH:29][CH:28]=1)[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH3:18]>>[CH2:17]([O:19][C@@H:20]([CH2:26][C:27]1[CH:28]=[CH:29][C:30]([O:15][CH2:14]/[CH:13]=[C:12](/[C:9]2[CH:10]=[CH:11][C:6]([C:2]3[O:1][CH:5]=[CH:4][CH:3]=3)=[CH:7][CH:8]=2)\[CH3:16])=[CH:31][CH:32]=1)[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH3:18]

Participants

3

Reactant 2

HCID 9816147Ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoateHCID 69800884(E)-3-(4-furan-2-yl-phenyl)-but-2-en-1-ol

Product 1

HCID 86758944(E)-(S)-Ethyl 2-Ethoxy-3-{4-[3-(4-furan-2-yl-phenyl)-but-2-enyloxy]-phenyl}propionateYield 78%

Procedure

The title compound (678 mg, 77%) was prepared from (E)-3-(4-furan-2-yl-phenyl)-but-2-en-1-ol (430 mg, 2.0 mmol) and (S)-ethyl 2-ethoxy-3-(4-hydroxyphenyl)-propionate (526 mg, 2.21 mmol) by a procedure analogous to that described in example 52c.

Sources & evidence

ORD record
ord-02c07df859d7430ba84ac1374928e5c6
Source dataset
uspto-grants-2003_04
Patent number
US06555577B1

Reaction notes

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