Water → (8-Methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl)methyl 4-methylbenzene-1-sulfonate

HRID 720375ノート

反応式

HRID 720375 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][C@@H:13]2[O:18][C:17]3[C:19](/[CH:26]=[CH:27]/[C:28](=O)[CH3:29])=[C:20]([N+:23]([O-])=O)[CH:21]=[CH:22][C:16]=3[O:15][CH2:14]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.O>C(O)(=O)C.C(O)C.[Fe]>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([O:11][CH2:12][CH:13]2[O:18][C:17]3=[C:19]4[C:20](=[CH:21][CH:22]=[C:16]3[O:15][CH2:14]2)[N:23]=[C:28]([CH3:29])[CH:27]=[CH:26]4)(=[O:10])=[O:9])=[CH:6][CH:7]=1

参加物

5

反応物 2

HCID 962WaterHCID 12082210{(2R)-7-nitro-8-[(E)-3-oxo-1-butenyl]-2,3-dihydro-1,4-benzodioxin-2-yl}methyl 4-methylbenzenesulfonate

生成物 1

HCID 21892063(8-Methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl)methyl 4-methylbenzene-1-sulfonate

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 18476134Acetic acid ethanol溶媒

実験手順

To a solution of {(2R)-7-nitro-8-[(E)-3-oxo-1-butenyl]-2,3-dihydro-1,4-benzodioxin-2-yl}methyl 4-methylbenzenesulfonate (3.40 g, 7.83 mmole) in 200 mL of acetic acid/ethanol (3:2) was added 2.25 g (40.2 mmole) of iron powder and the mixture was heated at reflux under nitrogen for 8 hours. After the reaction was complete, 150 mL of water was added and the mixture filtered through a pad of celite. The filtrate was neutralized with saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The extract was dried over magnesium sulfate, filtered, and evaporated in vacuum. The residue was column chromatographed on silica gel using a gradient elution commencing with 20% ethyl acetate/hexane and ending with 70% ethyl acetate/hexane to give 2.5 g of the (R)-enantiomer of the title compound as a yellow oil. 1H-NMR (CDCl3): doublet 8.1 δ (1 H); doublet 7.6 δ (2 H); doublet 7.45 δ (1 H); multiplet 7.2 δ (4 H); multiplet 4.6 δ (1 H); multiplet 4.3 δ (3 H); multiplet 4.1 δ (1 H); singlet 2.5 δ (3H); singlet 2.4 δ (3 H).

後処理

  1. temperaturethe mixture was heated
  2. temperatureat reflux under nitrogen for 8 hours
  3. filtrationthe mixture filtered through a pad of celite
  4. extractionextracted with ethyl acetate
  5. dry with materialThe extract was dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuum
  8. customchromatographed on silica gel using a gradient elution commencing with 20% ethyl acetate/hexane

出典と根拠

ORDレコード
ord-60aba3dbd7044c5c877e30908e73280f
出典データセット
uspto-grants-2006_11
特許番号
US07135479B2

反応ノート

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