Tributylphosphine → (E)-(2S)-2-Ethoxy-3-{4-[3-(4-furan-2-yl-phenyl)-3-phenyl-allyloxy]-phenyl}-propionic acid ethyl ester

HRID 488436Notes

Reaction equation

HRID 488436 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](/[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:13]/[CH2:14][OH:15])=[CH:8][CH:7]=1.C(P(CCCC)CCCC)CCC.[CH2:35]([O:37][C:38](=[O:51])[C@@H:39]([O:48][CH2:49][CH3:50])[CH2:40][C:41]1[CH:46]=[CH:45][C:44](O)=[CH:43][CH:42]=1)[CH3:36]>C1C=CC=CC=1>[CH2:35]([O:37][C:38](=[O:51])[C@@H:39]([O:48][CH2:49][CH3:50])[CH2:40][C:41]1[CH:46]=[CH:45][C:44]([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)\[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:43][CH:42]=1)[CH3:36]

Participants

5

Reactant 3

HCID 13831TributylphosphineHCID 9816147Ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoateHCID 69774305(E)-3-(4-furan-2-yl-phenyl)-3-phenyl-prop-2-en-1-ol

Product 1

HCID 69774285(E)-(2S)-2-Ethoxy-3-{4-[3-(4-furan-2-yl-phenyl)-3-phenyl-allyloxy]-phenyl}-propionic acid ethyl esterYield 53%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Reaction of (E)-3-(4-furan-2-yl-phenyl)-3-phenyl-prop-2-en-1-ol (475 mg, 1.72 mmol), tributylphosphine (0.63 ml, 2.58 mmol), (2S)-2-ethoxy-3-(4-hydroxy-phenyl)-propionic acid ethyl ester (451 mg, 1.89 mmol) and azodicarboxylic dipiperidide (650 mg, 2.58 mmol) in benzene in an identical manner to example 3 gave the title compound (450 mg, 53%).

Sources & evidence

ORD record
ord-70b21f79b1144ee8b263bf11ed02fd13
Source dataset
uspto-grants-2005_12
Patent number
US06972294B1

Reaction notes

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