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

HRID 655929노트

반응식

HRID 655929 반응식
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]

참가 물질

5

반응물 2

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

생성물 1

HCID 44549250Methyl 3-formyl-2-nitrobenzoate

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

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)−.

후처리

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

출처 및 근거

ORD 기록
ord-37920e585387486098210fbc7ef8d449
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071623B2

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