Methyl morpholine oxide → Methyl 3-formyl-2-nitrobenzoate

HRID 655929Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 655929
Br[CH2:2][C:3]1[C:4]([N+:13]([O-:15])=[O:14])=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7].C[N+]1([O-])CC[O:20]CC1>CC#N.CCOC(C)=O>[CH:2]([C:3]1[C:4]([N+:13]([O-:15])=[O:14])=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])=[O:20]

Komponenten

5

Edukt 2

HCID 82029Methyl morpholine oxideHCID 22509333Methyl 3-(bromomethyl)-2-nitrobenzoate

Produkt 1

HCID 44549250Methyl 3-formyl-2-nitrobenzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of (A2) (1.0 eq.) and 4 Å mol. sieves (15 g) in MeCN (0.2M) at RT was added NMMO (2.0 eq.) and the reaction mixture was stirred for 1.5 hr under N2 atmosphere. Then, the mixture was diluted with EtOAc, filtered and the filtrate was washed with H2O, 1N HCl, brine and dried (Na2SO4). Evaporation of the solvent gave (A3) as a white solid which was used in the next step without further purification. 1H NMR (400 MHz, CDCl3, 300K) δ 9.96 (1H, s), 8.26 (1H, d, J=7.9 Hz), 8.18 (1H, d, J=7.9 Hz), 7.77 (1H, t, J=7.9 Hz), 3.93 (3H, s). MS (ES) C9H7NO5 requires: 209. Found: 208 (M−H)−.

Aufarbeitung

  1. filtrationfiltered
  2. washthe filtrate was washed with H2O, 1N HCl, brine
  3. dry with materialdried (Na2SO4)
  4. customEvaporation of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-37920e585387486098210fbc7ef8d449
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071623B2

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