Triethylamine → Ethyl 5-(morpholinomethyl)isoxazole-3-carboxylate

HRID 872782ノート

反応式

HRID 872782 の反応式
[CH3:1][CH2:2][O:3][C:4](/[C:6](/Cl)=[N:7]\[OH:8])=[O:5].[CH2:10]([N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)[C:11]#[CH:12].C(N(CC)CC)C>C1(C)C=CC=CC=1.O>[O:16]1[CH2:17][CH2:18][N:13]([CH2:10][C:11]2[O:8][N:7]=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH:12]=2)[CH2:14][CH2:15]1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 4129414-(2-Propyn-1-yl)morpholineHCID 6399471Ethyl 2-chloro-2-(hydroxyimino)acetate

生成物 1

HCID 23006302Ethyl 5-(morpholinomethyl)isoxazole-3-carboxylate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒2 回

実験手順

To the solution of ethyl chlorooximidoacetate (0.588 g, 3.88 mmol) and 4-(prop-2-ynyl)morpholine (0.971 g, 7.76 mmol) in toluene (5 mL) was added solution of triethylamine (0.54 mL, 3.88 mmol) in toluene (5 mL) dropwise. The resultant mixture was stirred at RT for 5 h. After the completion of the reaction as evidenced by LC-MS, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic solvent was then dried over anhydrous sodium sulfate and evaporated. The crude product was purified by Combiflash (Heptane:EtOAc eluent). Yield 0.2 g. 1H NMR (400 MHz; MeOD): δ 1.38 (t, 3H), 2.53 (m, 4H), 3.69 (m, 4H), 3.78 (d, 2H), 4.41 (q, 2H), 6.73 (m, 1H).

後処理

  1. customAfter the completion of the reaction
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic solvent was then dried over anhydrous sodium sulfate
  4. customevaporated
  5. customThe crude product was purified by Combiflash (Heptane:EtOAc eluent)

出典と根拠

ORDレコード
ord-7308ad297900412db1a4865e1737e70c
出典データセット
uspto-grants-2015_03
特許番号
US08975254B2

反応ノート

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