Reaction #2139938

Reaction equation

HCl

2,2,2-Trifluoro-1-(4-{3-[4-(2,2,2-trifluoro-1-hydroxyimino-ethyl)-phenoxy]-propoxy}-phenyl)-ethanone oxime

2,6-lutidine

2-chloroethanesulfonyl chloride

→

product

2,2,2-Trifluoro-1-(4-{3-[4-(2,2,2-trifluoro-1-vinylsulfonyloxyimino-ethyl)-phenoxy]-propoxy}-phenyl)-ethanone oxime vinylsulfonate

Solvents

CH2Cl2

Conditions

Workup

1. 1
   Otheris prepared
2. 2
   Temperaturethe solution is cooled in an ice-bath
3. 3
   ExtractionThe crude product is extracted with CH2Cl2
4. 4
   Washwashed with 1N HCl
5. 5
   Dryingdried over MgSO4
6. 6
   Concentrationconcentrated
7. 7
   OtherThe residue is purified by recrystallizaffon from methanol

Procedure

In 30 mL of CH2Cl2 are dissolved 3.0 g (6.66 mmol) of 2,2,2-Trifluoro-1-(4-{3-[4-(2,2,2-trifluoro-1-hydroxyimino-ethyl)-phenoxy]-propoxy}-phenyl)-ethanone oxime, which is prepared according to the method described in GB 2348644, and the solution is cooled in an ice-bath. To the solution are added successively 2,6-lutidine (3.5 mL, 30.0 mmol) and 2-chloroethanesulfonyl chloride (1.55 mL, 14.7 mmol), and the reaction solution is stirred at 0° C. for 1 h and at room temperature for 2.5 h. Then, it is poured into 1N HCl. The crude product is extracted with CH2Cl2, washed with 1N HCl, dried over MgSO4 and concentrated. The residue is purified by recrystallizaffon from methanol to afford the product as a beige solid. The structure is confirmed by the 1H-NMR spectrum (CDCl3). δ [ppm]: 2.32 (m, 2H), 4.23 (t, 4H), 6.32 (d, 2H), 6.61 (d, 2H), 6.72 (dd, 2H), 7.00 (d, 4H), 7.50 (d, 4H). mp. 84-88° C.

Source