Réaction #77632

ord-2c741ead76fc4fa6ad942e1ad7df089c

Équation de réaction

CCC(=O)c1cc(CCc2ccc(CO[Si](C)(C)C(C)(C)C)c(CO[Si](C)(C)C(C)(C)C)c2)cs1
1-{4-[2-(3,4-bis(tert-butyldimethylsilanyloxymethyl)phenyl)ethyl]-2-thienyl}-1-propanone
O=C(O)CCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-]
(3-carboxy-propyl)triphenylphosphonium bromide
CC(C)(C)[O-].[K+]
potassium tert-butoxide
→
CC/C(=C\CCC(=O)O)c1cc(CCc2ccc(CO[Si](C)(C)C(C)(C)C)c(CO[Si](C)(C)C(C)(C)C)c2)cs1
desired product
CC/C(=C\CCC(=O)O)c1cc(CCc2ccc(CO[Si](C)(C)C(C)(C)C)c(CO[Si](C)(C)C(C)(C)C)c2)cs1
(E)-5-{4-[2-(3,4-bis(tert-Butyldimethylsilanyloxy-methyl)phenyl)ethyl]-2-thienyl}-4-heptenoic Acid

Réactifs

CCC(=O)c1cc(CCc2ccc(CO[Si](C)(C)C(C)(C)C)c(CO[Si](C)(C)C(C)(C)C)c2)cs1
1-{4-[2-(3,4-bis(tert-butyldimethylsilanyloxymethyl)phenyl)ethyl]-2-thienyl}-1-propanone
O=C(O)CCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-]
(3-carboxy-propyl)triphenylphosphonium bromide
CC(C)(C)[O-].[K+]
potassium tert-butoxide

Réactifs

Aucun

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Mode opératoire

In a manner similar to that of Example 6(i), by reaction of 3 g (5.6 mmol) of 1-{4-[2-(3,4-bis(tert-butyldimethylsilanyloxymethyl)phenyl)ethyl]-2-thienyl}-1-propanone with 3.6 g (8.4 mmol) of (3-carboxy-propyl)triphenylphosphonium bromide and 1.9 g (17 mmol) of potassium tert-butoxide, the desired product is obtained in the form of a yellow oil (m=1.7 g, Y=50%).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US06706725B1uspto-grants-2004_03