Reacción #1687656

Ecuación de reacción

KOH

2,6-dihydroxynaphthalene

diethyl(4-bromobutyl)phosphonate

→

2,6Bis(4-phosphonobutyloxy)-naphthalene

Disolventes

ethanol

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITthe mixture was left at room temperature for over night
2. 2
   ExtracciónThe product was extracted with CH2Cl2
3. 3
   SecadoThe CH2Cl2 solution was dried
4. 4
   Otroleaving a brownish solid
5. 5
   OtroThe ester was purified by column chromatography
6. 6
   workup.ADDITIONfollowed by addition of water
7. 7
   LavadoThe bisphosphonic acid derivative was washed with CH2Cl2
8. 8
   Filtraciónfiltered
9. 9
   Otrocollected

Procedimiento

1.34 g of KOH in ethanol were added dropwise to a mixture of 2,6-dihydroxynaphthalene (1.6g, 10 mmol) and diethyl(4-bromobutyl)phosphonate (6.0 g, 22 mmol) in ethanol, the mixture was left at room temperature for over night. The product was extracted with CH2Cl2. The CH2Cl2 solution was dried, leaving a brownish solid. The ester was purified by column chromatography. The bisphosphonate ester was converted to the acid by overnight stirring with 4-fold excess of bromotrimethylsilane in dry dichloromethane followed by addition of water. The bisphosphonic acid derivative was washed with CH2Cl2, filtered and collected.

Fuente