Réaction #43467

Équation de réaction

compound 7A

Methyl 3-chloro-4-cyano-2-methylbenzoate

1,2-ethanedithiol

→

title compound

Rendement 66.5%

2-Chloro-4-(hydroxymethyl)-3-methylbenzonitrile

Rendement 66.5%

Solvants

THF

Conditions de réaction

Traitement

1. 1
   AutreTo a pressure reaction flask
2. 2
   AutreIt was sealed
3. 3
   Températurecooled to RT
4. 4
   ConcentrationThe reaction mixture was concentrated
5. 5
   workup.DISSOLUTIONdissolved in EtOAc
6. 6
   Lavagewashed with water
7. 7
   Séchagedried over Na2SO4
8. 8
   Concentrationconcentrated
9. 9
   AutreRecrystallization in EtOAc/hexanes

Mode opératoire

To a pressure reaction flask containing compound 7A (1.5 g, 7.2 mmol) in THF (30 mL) were added 1,2-ethanedithiol (2.4 g, 28.6 mmol) and NaBH (812 mg, 21.5 mmol). It was sealed, and heated at 70° C. for 2 hr, and cooled to RT. The reaction mixture was concentrated, dissolved in EtOAc, washed with water, dried over Na2SO4, and concentrated. Recrystallization in EtOAc/hexanes give the title compound (870 mg). (ES) m/z 182 [M+H]+; 204 [M+Na]+.

Source