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

HRID 2090523ノート

反応式

HRID 2090523 の反応式
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]

参加物

5

反応物 2

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

生成物 1

HCID 44549250Methyl 3-formyl-2-nitrobenzoate

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a mixture of (A2) (1.0 eq.) and 4 Å mol. sieves 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)−.

後処理

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

出典と根拠

ORDレコード
ord-3535cbaaecad43648411f387e8ac55b5
出典データセット
uspto-grants-2013_05
特許番号
US08436185B2

反応ノート

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