Triphenylphosphine → (E)-(S)-ethyl 3-[4-(3-biphenyl-4-yl-but-2-enyloxy)-phenyl]-2-ethoxy-propionate
Reaction equation
N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:32]1([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH:37]=[CH:36][C:35](/[C:38](/[CH3:42])=[CH:39]/[CH2:40][OH:41])=[CH:34][CH:33]=1.[CH2:49]([O:51][C@@H:52]([CH2:58][C:59]1[CH:64]=[CH:63][C:62](O)=[CH:61][CH:60]=1)[C:53]([O:55][CH2:56][CH3:57])=[O:54])[CH3:50]>C1COCC1>[C:32]1([C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH:33]=[CH:34][C:35](/[C:38](/[CH3:42])=[CH:39]/[CH2:40][O:41][C:62]2[CH:61]=[CH:60][C:59]([CH2:58][C@H:52]([O:51][CH2:49][CH3:50])[C:53]([O:55][CH2:56][CH3:57])=[O:54])=[CH:64][CH:63]=2)=[CH:36][CH:37]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Diethyl azodicarboxylate (0.346 ml, 2.2 mmol) was added at 0° C. to a stirred solution of triphenyl-phosphine (0.656 g, 2.2 mmol) and (E)-3-biphenyl-4-yl-but-2-en-1-ol (0.270 g, 1.2 mmol) in dry THF (20 ml) and the mixture stirred for 5 min. A solution of (S)-ethyl 2-ethoxy-3-(4-hydroxy-phenyl)-propionate (0.238 g, 1.0 mmol) in dry THF (10 ml) was added, the mixture allowed to warm to room temperature, and stirring continued for 48 h. The resulting mixture was evaporated in vacuo and the residue purified by column chromatography on silica gel (20% ethyl acetate in n-heptane) to give (E)-(S)-ethyl 3-[4-(3-biphenyl-4-yl-but-2-enyloxy)-phenyl]-2-ethoxy-propionate as an oil; 0.288 g (65%).
Workup
- stirringstirring
- waitcontinued for 48 h
- customThe resulting mixture was evaporated in vacuo
- customthe residue purified by column chromatography on silica gel (20% ethyl acetate in n-heptane)
Sources & evidence
- ORD record
- ord-cdd8ee1ee5b845689f13e060d292dbc2
- Source dataset
- uspto-grants-2003_04
- Patent number
- US06555577B1
Reaction notes
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