反応 #10281

反応方程式

phosgene

5-chloro-1-pentanol

N,N-diethylaniline

4-aminobutyraldehyde diethylacetal

triethylamine

→

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

溶媒

toluene

toluene

ethyl acetate

反応条件

後処理

1. 1
   ろ過The mixture was filtered
2. 2
   濃縮the filtrate was concentrated
3. 3
   ろ過filtered
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
   ろ過filtered
7. 7
   濃縮concentrated
8. 8
   その他Purification by silica gel chromatography
9. 9
   洗浄eluting with 10% ethyl acetate in hexane

実験手順

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.

出典