Reacción #10281

Ecuación de reacción

phosgene

5-chloro-1-pentanol

N,N-diethylaniline

4-aminobutyraldehyde diethylacetal

triethylamine

→

(4,4-diethoxybutyl)carbamic acid 5-chloro-pentyl ester

Disolventes

toluene

toluene

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   FiltraciónThe mixture was filtered
2. 2
   Concentraciónthe filtrate was concentrated
3. 3
   Filtraciónfiltered
4. 4
   workup.ADDITIONthe solution was added dropwise to an ice-
5. 5
   workup.STIRRINGThe reaction mixture was stirred at room temperature for 15 hours
6. 6
   Filtraciónfiltered
7. 7
   Concentraciónconcentrated
8. 8
   OtroPurification by silica gel chromatography
9. 9
   Lavadoeluting with 10% ethyl acetate in hexane

Procedimiento

To an ice-cooled solution of 1.93M phosgene in toluene (31 mL, 60 mmole) was added dropwise a solution of 5-chloro-1-pentanol (4.9 g, 40 mmole) and N,N-diethylaniline (5.97 g, 40 mmole) in toluene (40 mL). The reaction mixture was stirred at ambient temperature for 4 hours. The mixture was filtered, and the filtrate was concentrated. The residue was taken up in ethyl acetate, filtered, and the solution was added dropwise to an ice-cooled solution of 4-aminobutyraldehyde diethylacetal (7.09 g, 44 mmole) and triethylamine (4.45 g, 44 mmole) in ethyl acetate (60 mL). The reaction mixture was stirred at room temperature for 15 hours, filtered and concentrated. Purification by silica gel chromatography, eluting with 10% ethyl acetate in hexane, gave (4,4-diethoxybutyl)carbamic acid 5-chloro-pentyl ester (11.4 g,) as an oil.

Fuente