반응 #1178419

반응 방정식

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

수율 101.2%

용매

CH2Cl2

반응 조건

후처리

1. 1
   workup.STIRRINGthe mixture was stirred for 0.5 h
2. 2
   추출The mixture was extracted with ether (150 mL)
3. 3
   추출The ether extract
4. 4
   세척was washed with saturated aqueous NaHCO3 (50 mL)
5. 5
   기타dried
6. 6
   기타evaporated under reduced pressure

실험 절차

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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