반응 #58878

반응 방정식

(5R)-5-benzyl-2,2,3-trimethyl imidazolidin-4-one

N-fluorobenzenesulfonimide

acetone

(3-bromophenyl)acetaldehyde

→

(R)-2-fluro-2-(3-bromophenyl)acetaldehyde

용매

ether

isopropanol

반응 조건

후처리

1. 1
   온도cooled to −78° C.
2. 2
   여과filtered through a pad of celite
3. 3
   세척The filtercake is washed with additional ether
4. 4
   workup.ADDITIONThe combined filtrates are treated with methylsulfide (5 mL)
5. 5
   세척washed with saturated NaHCO3 and brine
6. 6
   건조dried over MgSO4
7. 7
   농축concentrated under reduced pressure

실험 절차

A homogeneous mixture of (5R)-5-benzyl-2,2,3-trimethyl imidazolidin-4-one dichloroaccetic acid salt (97 mg, 0.4 mmol) and N-fluorobenzenesulfonimide (3.15 g, 10 mmol) in a 9:1 mixture of acetone and isopropanol at room temperature is treated with (3-bromophenyl)acetaldehyde (280 mg, 1.4 mmol), stirred for 1 h at room temperature, cooled to −78° C., diluted with ether, and filtered through a pad of celite. The filtercake is washed with additional ether. The combined filtrates are treated with methylsulfide (5 mL), washed with saturated NaHCO3 and brine, dried over MgSO4 and concentrated under reduced pressure to give (R)-2-fluro-2-(3-bromophenyl)acetaldehyde.

출처