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

HRID 33780
ノート
印刷プレビュー

反応式

HRID 33780 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

HCID 66052622-Chloro-6-morpholinopyran-4-one収率 75.4%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-39173e7f8abd44aa9174da35c16bc802
出典データセット
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07429660B2

反応ノート

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