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

HRID 1268321Notes

Reaction equation

HRID 1268321 reaction equation
[OH:1][CH2:2]/[CH:3]=[C:4](/[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18](=[O:20])[CH3:19])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)\[CH3:5].[CH2:21]([O:23][C@@H:24]([CH2:30][C:31]1[CH:36]=[CH:35][C:34](O)=[CH:33][CH:32]=1)[C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH3:22]>>[C:18]([C:15]1[CH:14]=[CH:13][C:12]([C:9]2[CH:10]=[CH:11][C:6](/[C:4](/[CH3:5])=[CH:3]/[CH2:2][O:1][C:34]3[CH:33]=[CH:32][C:31]([CH2:30][C@H:24]([O:23][CH2:21][CH3:22])[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:36][CH:35]=3)=[CH:7][CH:8]=2)=[CH:17][CH:16]=1)(=[O:20])[CH3:19]

Participants

3

Reactant 2

HCID 9816147Ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoateHCID 11425603(E)-1-[4'-(3-hydroxy-1-methyl-propenyl)-biphenyl-4-yl]-ethanone

Product 1

HCID 86589958(E)-(S)-ethyl 3-{4-[3-(4'-acetyl-biphenyl-4-yl)-but-2-enyloxy]-phenyl}-2-ethoxy-propionateYield 75.4%

Procedure

The title compound (275 mg, 75%) was prepared from (E)-1-[4′-(3-hydroxy-1-methyl-propenyl)-biphenyl-4-yl]-ethanone (200 mg, 0.75 mmol) and (S)-ethyl 2-ethoxy-3-(4-hydroxyphenyl)-propionate (188 mg, 0.79 mmol) by a procedure analogous to that described in example 52c.

Sources & evidence

ORD record
ord-5cc16ccecd7a49daad969748c21694c2
Source dataset
uspto-grants-2003_04
Patent number
US06555577B1

Reaction notes

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