تفاعل #2139940

معادلة التفاعل

triethylamine

N-hydroxy-5-norbornene-2,3-dicarboximide

2-chloroethanesulfonyl chloride

triethylamine

cyclohexanethiol

→

product

المردود 79.7%

N-(2-cyclohexylsulfanyl-ethanesulfonyloxy)-5-norbornene-2,3-dicarboximide

المردود 79.7%

المذيبات

water

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwhile cooling over an ice-bath
2. 2
   workup.ADDITIONis added first
3. 3
   استخلاصextracted two times with ethyl acetate (300 ml)
4. 4
   غسيلThe combined organic phases are washed with water (300 ml)
5. 5
   تجفيفdried over MgSO4
6. 6
   تركيزconcentrated
7. 7
   أخرىThe residue is purified by flash chromatography on silica gel with hexane and ethyl acetate (7:3) as eluent

الإجراء التجريبي

A solution of 5.38 g (30.0 mmol) of N-hydroxy-5-norbornene-2,3-dicarboximide in THF (75 ml) is treated successively with 2-chloroethanesulfonyl chloride (3.47 ml, 33.0 mmol) and triethylamine (9.6 ml, 69.0 mmol) while cooling over an ice-bath. After stirring for 1 h at 0° C. triethylamine (6.3 ml, 45.0 mmol) is added first, followed by the addition of cyclohexanethiol (4.05 ml, 33.0 mmol). The beige suspension is further stirred for 1 h at room temperature, then poured into water (140 ml) and extracted two times with ethyl acetate (300 ml). The combined organic phases are washed with water (300 ml), dried over MgSO4, and concentrated. The residue is purified by flash chromatography on silica gel with hexane and ethyl acetate (7:3) as eluent, yielding 9.22 g of the product as a white solid. The, structure is confirmed by the 1H-NMR spectrum (CDCl3). δ [ppm]: 1.21-1.40 (m, 6H), 1.50-1.56 (m, 1H), 1.58-1.67 (m, 1H), 1.74-1.85 (m, 3H), 1.92-2.04 (m, 2H), 2.67-2.79 (m, 1H), 3.03-3.11 (m, 2H), 3.34 (s, 2H), 3.48 (s, 2H), 3.62-3.70 (m, 2H), 6.19 (s, 2H). mp. 96-98° C.

المصدر