Tributylphosphine → (Z)-(S)-2-ethoxy-3-[4-(3-methyl-5-phenyl-pent-2-en-4-ynyloxy)-phenyl]-propionic acid ethyl ester
Reaction equation
N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C(P(CCCC)CCCC)CCC.[CH3:32]/[C:33](/[C:37]#[C:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[CH:34]/[CH2:35][OH:36].[CH2:45]([O:47][C@@H:48]([CH2:54][C:55]1[CH:60]=[CH:59][C:58](O)=[CH:57][CH:56]=1)[C:49]([O:51][CH2:52][CH3:53])=[O:50])[CH3:46]>C1C=CC=CC=1>[CH2:52]([O:51][C:49](=[O:50])[C@@H:48]([O:47][CH2:45][CH3:46])[CH2:54][C:55]1[CH:60]=[CH:59][C:58]([O:36][CH2:35]/[CH:34]=[C:33](/[CH3:32])\[C:37]#[C:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[CH:57][CH:56]=1)[CH3:53]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
1,1′-(azodicarbonyl) dipiperidine (0.504 g, 2.0 mmol) was added at 0° C. to a stirred solution of tributylphosphine (0.493 mL, 2.0 mmol), (Z)-3-methyl-5-phenyl-pent-2-en-4-yn-1-ol (0.172 g, 1.0 mmol) (J. Org. Chem. 1999, 64 (21), 7687-7692), and (S)-ethyl 2-ethoxy-3-(4-hydroxyphenyl)-propionate (0.262 g, 1.1 mmol) in dry benzene (20 mL), the mixture allowed to warm to room temperature, and stirring continued for 24 h. The resulting mixture was evaporated in vacuo, and the residue purified by flash column chromatography on silica gel (20% ethyl acetate in n-heptane eluent) to give (Z)-(S)-2-ethoxy-3-[4-(3-methyl-5-phenyl-pent-2-en-4-ynyloxy)-phenyl]-propionic acid ethyl ester as an oil; 0.267 g (68%).
Workup
- customThe resulting mixture was evaporated in vacuo
- customthe residue purified by flash column chromatography on silica gel (20% ethyl acetate in n-heptane eluent)
Sources & evidence
- ORD record
- ord-887474af8a8c42a49519969c348508ee
- Source dataset
- uspto-grants-2003_05
- Patent number
- US06569901B2
Reaction notes
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