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

HRID 751481

反応式

HRID 751481 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-b2c7e790db074372a74aaf68d083ad01
出典データセット
uspto-grants-2008_07
特許番号
US07405305B2

関連ノート

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