Tributylphosphine → (2S)-3-[4-(3,3-Diphenyl-allyloxy)-phenyl]-2-ethoxy-propionic acid ethyl ester

HRID 488441Notes

Reaction equation

HRID 488441 reaction equation
[C:1]1([C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][CH2:9][OH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(P(CCCC)CCCC)CCC.[CH2:30]([O:32][C:33](=[O:46])[C@@H:34]([O:43][CH2:44][CH3:45])[CH2:35][C:36]1[CH:41]=[CH:40][C:39](O)=[CH:38][CH:37]=1)[CH3:31]>>[CH2:30]([O:32][C:33](=[O:46])[C@@H:34]([O:43][CH2:44][CH3:45])[CH2:35][C:36]1[CH:41]=[CH:40][C:39]([O:10][CH2:9][CH:8]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[CH:38][CH:37]=1)[CH3:31]

Participants

4

Reactant 3

HCID 13831TributylphosphineHCID 9816147Ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoateHCID 105364313,3-Diphenyl-2-propene-1-ol

Product 1

HCID 69775738(2S)-3-[4-(3,3-Diphenyl-allyloxy)-phenyl]-2-ethoxy-propionic acid ethyl esterYield 67.4%

Procedure

Reaction of 3,3-diphenyl-prop-2-en-1-ol (210 mg, 1.0 mmol), tributylphosphine (303 mg, 1.50 mmol), (2S)-2-ethoxy-3-(4-hydroxy-phenyl)-propionic acid ethyl ester (250 mg, 1.05 mmol) and azodicarboxylic dipiperidide (378 mg, 1.50 mmol) in an identical manner to example 3 gave the title compound (290 mg, 67%).

Sources & evidence

ORD record
ord-8425f49f76524ed2813253602e63c74b
Source dataset
uspto-grants-2005_12
Patent number
US06972294B1

Reaction notes

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