反应 #1605761

反应方程式

Iodomethane

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

NaOH

→

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

收率 73.1%

溶剂

DMF

DMF

反应条件

后处理

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

实验过程

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).

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