Reaktion #1178419

Reaktionsgleichung

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

Ausbeute 101.2%

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred for 0.5 h
2. 2
   ExtraktionThe mixture was extracted with ether (150 mL)
3. 3
   ExtraktionThe ether extract
4. 4
   Waschenwas washed with saturated aqueous NaHCO3 (50 mL)
5. 5
   Sonstigedried
6. 6
   Sonstigeevaporated under reduced pressure

Vorschrift

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).

Quelle