反応 #1178419

反応方程式

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

収率 101.2%

溶媒

CH2Cl2

反応条件

後処理

1. 1
   workup.STIRRINGthe mixture was stirred for 0.5 h
2. 2
   抽出The mixture was extracted with ether (150 mL)
3. 3
   抽出The ether extract
4. 4
   洗浄was washed with saturated aqueous NaHCO3 (50 mL)
5. 5
   その他dried
6. 6
   その他evaporated under reduced pressure

実験手順

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).

出典