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Sodium Hydroxide → 2-Chloro-6-morpholinopyran-4-one

HRID 33780
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HRID 33780 반응식
[Cl:1][C:2](Cl)=[CH:3][C:4](=[O:14])[CH2:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)=[O:7].Cl(O)(=O)(=O)=O.[OH-].[Na+]>O1CCOCC1>[Cl:1][C:2]1[O:7][C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:5][C:4](=[O:14])[CH:3]=1
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참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 24247Perchloric AcidHCID 66052615,5-Dichloro-1-morpholinopent-4-ene-1,3-dione

생성물 1

HCID 66052622-Chloro-6-morpholinopyran-4-one수율 75.4%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
90 °C

실험 절차

To a suspension of 2 (11.3 g, 44.9 mmol) in dioxane was added perchloric acid (11.4 ml, 0.14 mol) and the reaction was heated at 90° C. under N2 for 1 hour. The reaction was cooled, neutralised with 2M NaOH (75 ml) and filtered. The aqueous layer was extracted with DCM (4×30 ml) and the organic layers were combined and dried over MgSO4. The organic layer was further treated with charcoal and filtered through celite. The dark yellow filtrate was evaporated in vacuo, and the resulting solid was triturated with hexane (50 ml) and dried to give 3 (7.3 g, 75%) as a light yellow powder. m/z (LC-MS, ESP): 216 (M++1). 1H-NMR (300 MHz, DMSO-d6): 3.3 (t, 4H), 3.65 (t, 4H), 5.4 (d, 1H), 6.25 (d, 1H).

후처리

  1. temperatureThe reaction was cooled
  2. filtrationfiltered
  3. extractionThe aqueous layer was extracted with DCM (4×30 ml)
  4. dry with materialdried over MgSO4
  5. additionThe organic layer was further treated with charcoal
  6. filtrationfiltered through celite
  7. customThe dark yellow filtrate was evaporated in vacuo
  8. customthe resulting solid was triturated with hexane (50 ml)
  9. customdried

출처 및 근거

ORD 기록
ord-39173e7f8abd44aa9174da35c16bc802
출처 데이터셋
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07429660B2

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