Réaction #1605761

Équation de réaction

Iodomethane

(R)—N-(1-hydroxy-4-methylpentan-2-yl)-3,4-dimethylbenzamide

NaOH

→

(R)—N-(1-methoxy-4-methylpentan-2-yl)-3,4-dimethylbenzamide

Rendement 73.1%

Solvants

DMF

DMF

Conditions de réaction

Traitement

1. 1
   Autrewas kept at 0° C.
2. 2
   workup.STIRRINGthe mixture was stirred for 1 hr
3. 3
   AutreThe reaction was quenched
4. 4
   workup.ADDITIONby adding 300 ml of water
5. 5
   ExtractionThe aqueous layer was extracted with dichloromethane
6. 6
   Séchagedried over MgSO4
7. 7
   Autreevaporated
8. 8
   AutreThe residue was purified by flash chromatography on silica-gel (toluene-ethyl acetate; 5-20% gradient)

Mode opératoire

To a solution of (R)—N-(1-hydroxy-4-methylpentan-2-yl)-3,4-dimethylbenzamide (1.59 g, 6.39 mmol) (example 18a) in dry DMF (20 mL) was added powdered NaOH (281 mg, 7 mmol) an the solution was stirred at 0° C. for 2 hrs. Iodomethane (1 eq, 6.39 mmol) was added in DMF (10 ml) drop-wise over period of 1 hr. The temperature was kept at 0° C. and the mixture was stirred for 1 hr. The reaction was quenched by adding 300 ml of water. The aqueous layer was extracted with dichloromethane, dried over MgSO4 and evaporated. The residue was purified by flash chromatography on silica-gel (toluene-ethyl acetate; 5-20% gradient) to give 1.23 g (R)—N-(1-methoxy-4-methylpentan-2-yl)-3,4-dimethylbenzamide (73%). 1H NMR (500 MHz, CDCl3): ÿ 0.94-0.97 (t, 6H), 1.41-1.47 (M, 1H), 1.54-1.60 (m, 1H), 1.64-1.68 (m, 1H), 2.29 (d, 6H)5 3.36 (s3 3H), 3.45-3.50 (m, 2H), 4.34-4.39 (m, 1H), 6.23-6.25 (d, 1H), 7.16-7.17 (d, 1H), 7.47-7.49 (dd, 1H), 7.56 (s, 1H). MS (M+H, 264.3).

Source