反応 #64654

反応方程式

title compound

phenylmethyl α-methylenebenzenepropanoate

2-dimethylaminoethanethiol hydrochloride

piperidine

benzyltrimethylammonium hydroxide

→

title compound

収率 24.0%

phenylmethyl α-[[[2-(dimethylamino)ethyl]thio]methyl]benzene-propanoate

収率 24.0%

溶媒

methanol

MeOH

反応条件

後処理

1. 1
   その他The solvent was removed on a rotary evaporator
2. 2
   その他the residue was purified by flash chromotography on silica gel
3. 3
   洗浄eluting with 20:1 CH2Cl2

実験手順

The title compound of Step 10 (1.5 g, 5.95 mmol) was dissolved under argon in methanol (22 mL). To this solution was added 2-dimethylaminoethanethiol hydrochloride (843 mg, 5.95 mmol), piperidine (0.78 mL, 7.85 mmol) and benzyltrimethylammonium hydroxide (0.25 mL, 0.6 mmol), and the mixture was stirred at room temperature for 16 hours. The solvent was removed on a rotary evaporator and then the residue was purified by flash chromotography on silica gel, eluting with 20:1 CH2Cl2 :MeOH to give the pure title compound (0.5 g, 24% yield). 1H NMR: 300 MHz spectrum consistent with proposed structure. Anal: calcd. for C21H27NO2S+0.2H2O: C, 69.85; H, 7.65; N, 3.88. Found: C, 69.58; H, 7.60; N, 3.98.

出典