Water → 2,3-Dihydro[1,4]dioxino[2,3-f]quinolin-2-ylmethyl4-methylbenzenesulfonate

HRID 2056359노트

반응식

HRID 2056359 반응식
[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][CH:28]=O)=[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:7]=[CH:6][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]=[CH:28][CH:27]=[CH:26]4)(=[O:9])=[O:10])=[CH:4][CH:3]=1

참가 물질

5

반응물 2

HCID 962WaterHCID 86586348{(2R)-7-nitro-8-[3-oxo-1-propenyl]-2,3-dihydro-1,4-benzodioxin-2-yl}methyl4-methylbenzenesulfonate

생성물 1

HCID 218920582,3-Dihydro[1,4]dioxino[2,3-f]quinolin-2-ylmethyl4-methylbenzenesulfonate

시약·촉매·용매 2

HCID 23925Iron촉매HCID 18476134Acetic acid ethanol용매

실험 절차

To a solution of {(2R)-7-nitro-8-[3-oxo-1-propenyl]-2,3-dihydro-1,4-benzodioxin-2-yl}methyl 4-methylbenzenesulfonate (3.50 g, 8.35 mmole) in 200 mL of acetic acid/ethanol (1:1) was added 2.35 g (42.1 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 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 1.85 g of the (R)-enantiomer of the title compound as a yellow oil. 1H-NMR (CDCl3): doublet 8.8 δ (1 H); doublet 8.2 δ (1 H); doublet 7.8 δ (2 H); doublet 7.6 δ (1 H); multiplet 7.35 δ (1 H); multiplet 7.25 δ (3 H); multiplet 4.6 δ (1 H); multiplet 4.3-4.4 δ (3 H); multiplet 4.2 δ (1 H); singlet 2.4 δ (3 H).

후처리

  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

출처 및 근거

ORD 기록
ord-e052d7c4dd0441e2bc41041ecac33600
출처 데이터셋
uspto-grants-2008_02
특허 번호
US07335666B2

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