Dimethylformamide → 1-(2,2-Dimethoxyethyl)-3-methyl-2-nitrobenzene

HRID 751481노트

반응식

HRID 751481 반응식
[N+:1]([C:4]1[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][C:5]=1[CH3:11])([O-:3])=[O:2].[CH3:12][O:13][CH:14]([O:18][CH3:19])N(C)C.CN(C)C=O.C[Si](Cl)(C)C>C(OCC)(=O)C.CO>[CH3:12][O:13][CH:14]([O:18][CH3:19])[CH2:11][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]([CH3:10])[C:4]=1[N+:1]([O-:3])=[O:2]

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 6397ChlorotrimethylsilaneHCID 66722,6-DimethylnitrobenzeneHCID 78373Dimethylformamide dimethyl acetal

생성물 1

HCID 692699561-(2,2-Dimethoxyethyl)-3-methyl-2-nitrobenzene수율 14%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8857Ethyl Acetate용매

실험 절차

Combine 2-nitro-meta-xylene (5 mL, 0.037 mol), N,N-dimethylformamide dimethylacetal (5.4 mL, 1.1 eq) and N,N-dimethylformamide (60 mL) in a flask and reflux under nitrogen for 2 days. Let cool to room temperature then concentrate to approximately one-half volume. Add methanol (40 mL) and trimethylsilylchloride (6.6 mL, 1.4 eq). Reflux overnight. Dilute with ethyl acetate after cooling to room temperature then extract with saturated sodium bicarbonate followed by brine. Dry over magnesium sulfate, filter and concentrate. Purification by column chromatography (9:1 Hexanes:ethyl acetate) gives 1.15 g (14%) product as a light yellow oil. 1H NMR (400 MHz, DMSO-d6) δ 2.23 (s, 3H), 2.80 (d, J=5.36 Hz, 2H), 3.19 (s, 6H), 4.45 (m, 1H), 7.32 (m, 2H), 7.42 (m, 1H).

후처리

  1. concentrationthen concentrate to approximately one-half volume
  2. temperatureReflux overnight
  3. temperatureafter cooling to room temperature
  4. extractionthen extract with saturated sodium bicarbonate
  5. dry with materialDry over magnesium sulfate
  6. filtrationfilter
  7. concentrationconcentrate
  8. customPurification by column chromatography (9:1 Hexanes:ethyl acetate)

출처 및 근거

ORD 기록
ord-b2c7e790db074372a74aaf68d083ad01
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07405305B2

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