تفاعل #1605761

معادلة التفاعل

Iodomethane

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

NaOH

→

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

المردود 73.1%

المذيبات

DMF

DMF

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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).

المصدر