Tributylphosphine → 3-{4-[3,3-Bis-(3-methyl-thiophen-2-yl)-allyloxy]-phenyl}-2-ethoxy-propionic acid ethyl ester

HRID 488438Notes

Reaction equation

HRID 488438 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([C:11]1[S:12][CH:13]=[CH:14][C:15]=1[CH3:16])=[CH:8][CH2:9][OH:10].C(P(CCCC)CCCC)CCC.[CH2:30]([O:32][C:33](=[O:46])[CH: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])[CH: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:11]2[S:12][CH:13]=[CH:14][C:15]=2[CH3:16])[C:3]2[S:4][CH:5]=[CH:6][C:2]=2[CH3:1])=[CH:38][CH:37]=1)[CH3:31]

Participants

4

Reactant 3

HCID 13831TributylphosphineHCID 11791243Ethyl 2-ethoxy-3-(4-hydroxyphenyl)propanoateHCID 219076783,3-Bis-(3-methylthiophen-2-yl)-prop-2-en-1-ol

Product 1

HCID 538376603-{4-[3,3-Bis-(3-methyl-thiophen-2-yl)-allyloxy]-phenyl}-2-ethoxy-propionic acid ethyl esterYield 36.2%

Procedure

Reaction of 3,3-bis-(3-methylthiophen-2-yl)-prop-2-en-1-ol (1.0 mg, 3.99 mmol), tributylphosphine (0.91 g, 4.5 mmol), 2-ethoxy-3-(4-hydroxy-phenyl)-propionic acid ethyl ester (1.07 g, 4.5 mmol) and azodicarboxylic dipiperidide (1.14 g, 4.5 mmol) in an identical manner to example 3 gave the title compound (680 mg, 36%).

Sources & evidence

ORD record
ord-087df995dfe74c39a97ce888501d4afb
Source dataset
uspto-grants-2005_12
Patent number
US06972294B1

Reaction notes

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