Реакция #1178419

Уравнение реакции

Na2S2O3

NaHCO3

N-(1-hydroxymethyl-1,2-dimethyl-propyl)-3-methoxy-2-methyl-benzamide

Dess-Martin periodinane

→

N-(1-formyl-1,2-dimethyl-propyl)-3-methoxy-2-methyl-benzamide

Выход 101.2%

Растворители

CH2Cl2

Условия реакции

Обработка

1. 1
   workup.STIRRINGthe mixture was stirred for 0.5 h
2. 2
   ЭкстракцияThe mixture was extracted with ether (150 mL)
3. 3
   ЭкстракцияThe ether extract
4. 4
   Промывкаwas washed with saturated aqueous NaHCO3 (50 mL)
5. 5
   Другоеdried
6. 6
   Другоеevaporated under reduced pressure

Методика

To a stirred solution of N-(1-hydroxymethyl-1,2-dimethyl-propyl)-3-methoxy-2-methyl-benzamide (X, R1=2-Me-3-MeO-Ph, R2=i-Pr, R3=Me, 285 mg, 1.1 mmol) in CH2Cl2 (10 mL) at room temperature was added Dess-Martin periodinane solution (15% by weight, 2.4 mL, ca. 1.1 mmol). The mixture was stirred at room temperature for 4 h and poured into saturated aqueous NaHCO3 (50 mL). Solid Na2S2O3 (2.13 g, 8.6 mmol) was added and the mixture was stirred for 0.5 h. The mixture was extracted with ether (150 mL). The ether extract was washed with saturated aqueous NaHCO3 (50 mL), dried and evaporated under reduced pressure to afford N-(1-formyl-1,2-dimethyl-propyl)-3-methoxy-2-methyl-benzamide (293 mg) as an oil. 1H NMR (CDCl3) δ (ppm): 0.98 (d, J=6.6 Hz, 3H), 1.04 (d, J=6.6 Hz, 3H), 1.51 (s, 3H), 2.27 (s, 3H), 2.29 (m, 1H), 3.84 (s, 3H), 6.30 (br s, 1H), 6.91 (m, 1H), 6.96 (m, 1H), 7.18 (m, 1H), 9.60 (s, 1H).

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