Tributylphosphine → HCID 69774053, compound

HRID 488445Notes

Reaction equation

HRID 488445 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)=[CH:9][CH2:10][OH:11])=[CH:4][CH:3]=1.C(P(CCCC)CCCC)CCC.[CH2:32]([O:34][C:35](=[O:48])[C@@H:36]([O:45][CH2:46][CH3:47])[CH2:37][C:38]1[CH:43]=[CH:42][C:41](O)=[CH:40][CH:39]=1)[CH3:33]>>[CH2:32]([O:34][C:35](=[O:48])[C@@H:36]([O:45][CH2:46][CH3:47])[CH2:37][C:38]1[CH:43]=[CH:42][C:41]([O:11][CH2:10][CH:9]=[C:8]([C:12]2[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=2)[C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=2)=[CH:40][CH:39]=1)[CH3:33]

Participants

4

Reactant 3

HCID 13831TributylphosphineHCID 9816147Ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoateHCID 22270319HCID 22270319, compound

Product 1

HCID 69774053HCID 69774053, compoundYield 39.5%

Procedure

Reaction of 3,3-di-(4-methylphenyl)-prop-2-en-1-ol (1.0 g, 4.20 mmol), tributylphosphine (1.27 g, 6.30 mmol), (2S)-2-ethoxy-3-(4-hydroxy-phenyl)-propionic acid ethyl ester (1.10 g, 4.62 mmol) and azodicarboxylic dipiperidide (1.59 g, 6.30 mmol) in an identical manner to example 3 gave the title compound (0.76 g, 39%).

Sources & evidence

ORD record
ord-32f5628e57dd48f4a924e519280ce1b2
Source dataset
uspto-grants-2005_12
Patent number
US06972294B1

Reaction notes

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