Ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoate → (E)-(S)-ethyl 3-{4-[3-(3',5'-bis-trifluoromethyl-biphenyl-4-yl)-but-2-enyloxy]-phenyl}-2-ethoxy-propionate

HRID 984371Notes

Reaction equation

HRID 984371 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:4]=[C:5]([C:13]2[CH:18]=[CH:17][C:16](/[C:19](/[CH3:23])=[CH:20]/[CH2:21][OH:22])=[CH:15][CH:14]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH2:26]([O:28][C@@H:29]([CH2:35][C:36]1[CH:41]=[CH:40][C:39](O)=[CH:38][CH:37]=1)[C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH3:27]>>[F:1][C:2]([F:24])([F:25])[C:3]1[CH:4]=[C:5]([C:13]2[CH:14]=[CH:15][C:16](/[C:19](/[CH3:23])=[CH:20]/[CH2:21][O:22][C:39]3[CH:38]=[CH:37][C:36]([CH2:35][C@H:29]([O:28][CH2:26][CH3:27])[C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:41][CH:40]=3)=[CH:17][CH:18]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

3

Reactant 2

HCID 9816147Ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoateHCID 20765801(E)-3-(3',5'-bis-trifluoromethyl-biphenyl-4-yl)-but-2-en-1-ol

Product 1

HCID 20765811(E)-(S)-ethyl 3-{4-[3-(3',5'-bis-trifluoromethyl-biphenyl-4-yl)-but-2-enyloxy]-phenyl}-2-ethoxy-propionateYield 81.3%

Procedure

The title compound (656 mg, 81%) was prepared as a colourless oil from (E)-3-(3′,5′-bis-trifluoromethyl-biphenyl-4-yl)-but-2-en-1-ol (500 mg, 1.39 mmol) and (S)-ethyl 2-ethoxy-3-(4-hydroxyphenyl)-propionate (348 mg, 1.46 mmol) by a procedure analogous to that described in example 52c.

Sources & evidence

ORD record
ord-468a3919e13144a3b1501d6ad43a1332
Source dataset
uspto-grants-2005_03
Patent number
US06867218B2

Reaction notes

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