Réaction #77616

ord-4b74ece7c24142998258a00b71333e48

Équation de réaction

CCC(=O)c1ccc(CCc2ccc(CO[Si](C)(C)C(C)(C)C)c(CO[Si](C)(C)C(C)(C)C)c2)s1
1-{5-[2-(3,4-bis(tert-butyldimethylsilanyloxymethyl)phenyl)ethyl]-2-thienyl}-1-propanone
O=C(O)CCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-]
(3-carboxypropyl)triphenylphosphonium bromide
CC(C)(C)[O-].[K+]
potassium tert-butoxide
→
CC/C(=C\CCC(=O)O)c1ccc(CCc2ccc(CO[Si](C)(C)C(C)(C)C)c(CO[Si](C)(C)C(C)(C)C)c2)s1
desired product
CC/C(=C\CCC(=O)O)c1ccc(CCc2ccc(CO[Si](C)(C)C(C)(C)C)c(CO[Si](C)(C)C(C)(C)C)c2)s1
(E)-5-{5-[2-(3,4-bis(tert-Butyldimethylsilanyloxy-methyl)phenyl)ethyl]-2-thienyl}-4-heptenoic Acid

Réactifs

CCC(=O)c1ccc(CCc2ccc(CO[Si](C)(C)C(C)(C)C)c(CO[Si](C)(C)C(C)(C)C)c2)s1
1-{5-[2-(3,4-bis(tert-butyldimethylsilanyloxymethyl)phenyl)ethyl]-2-thienyl}-1-propanone
O=C(O)CCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-]
(3-carboxypropyl)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 5.08 g (9.5 mmol) of 1-{5-[2-(3,4-bis(tert-butyldimethylsilanyloxymethyl)phenyl)ethyl]-2-thienyl}-1-propanone with 6.1 g (14 mmol) of (3-carboxypropyl)triphenylphosphonium bromide and 3.1 g (28 mmol) of potassium tert-butoxide, the desired product is obtained in the form of a yellow oil (m=2.7 g; Y=48%).

Source

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