Reaction #2139940

Reaction equation

triethylamine

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

2-chloroethanesulfonyl chloride

triethylamine

cyclohexanethiol

→

product

Yield 79.7%

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

Yield 79.7%

Solvents

water

THF

Conditions

Workup

1. 1
   Temperaturewhile cooling over an ice-bath
2. 2
   workup.ADDITIONis added first
3. 3
   Extractionextracted two times with ethyl acetate (300 ml)
4. 4
   WashThe combined organic phases are washed with water (300 ml)
5. 5
   Dryingdried over MgSO4
6. 6
   Concentrationconcentrated
7. 7
   OtherThe residue is purified by flash chromatography on silica gel with hexane and ethyl acetate (7:3) as eluent

Procedure

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.

Source