반응 #10281

반응 방정식

phosgene

5-chloro-1-pentanol

N,N-diethylaniline

4-aminobutyraldehyde diethylacetal

triethylamine

→

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

용매

toluene

toluene

ethyl acetate

반응 조건

후처리

1. 1
   여과The mixture was filtered
2. 2
   농축the filtrate was concentrated
3. 3
   여과filtered
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
   여과filtered
7. 7
   농축concentrated
8. 8
   기타Purification by silica gel chromatography
9. 9
   세척eluting with 10% ethyl acetate in hexane

실험 절차

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.

출처