Acetic Acid → ethyl 2-amino-4-(tetrahydro-4H-pyran-4-ylidene)butanoate

HRID 454447ノート

反応式

HRID 454447 の反応式
C1(C(=[N:14][CH:15]([CH2:21][CH:22]=[C:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[C:16]([O:18][CH2:19][CH3:20])=[O:17])C2C=CC=CC=2)C=CC=CC=1.O.C(O)(=O)C>C1COCC1>[NH2:14][CH:15]([CH2:21][CH:22]=[C:23]1[CH2:24][CH2:25][O:26][CH2:27][CH2:28]1)[C:16]([O:18][CH2:19][CH3:20])=[O:17]

参加物

5

反応物 3

HCID 176Acetic AcidHCID 962WaterHCID 58313138ethyl 2-[(diphenylmethylidene)amino]-4-(tetrahydro-4H-pyran-4-ylidene)butanoate

生成物 1

HCID 58313060ethyl 2-amino-4-(tetrahydro-4H-pyran-4-ylidene)butanoate収率 79.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of ethyl 2-[(diphenylmethylidene)amino]-4-(tetrahydro-4H-pyran-4-ylidene)butanoate (162) (6.8 g, 18.0 mmol) in THF (30 mL) was added water (30 mL) and glacial acetic acid (20 mL) and the reaction stirred at room temperature for 2.5 h. The reaction was concentrated in vacuo and the residue dissolved in 0.1 N HCl. It was extracted twice with ethyl acetate and the organic layer was discarded. To the aqueous layer was added solid potassium carbonate until the solution gave blue pH paper. The aqueous layer was extracted with 15% isopropanol/dichloromethane (3×) and the organic layer dried over sodium sulfate and concentrated in vacuo to afford the title compound as a clear oil (3.05 g, 79% yield).

後処理

  1. concentrationThe reaction was concentrated in vacuo
  2. dissolutionthe residue dissolved in 0.1 N HCl
  3. extractionIt was extracted twice with ethyl acetate
  4. additionTo the aqueous layer was added solid potassium carbonate until the solution
  5. customgave blue pH paper
  6. extractionThe aqueous layer was extracted with 15% isopropanol/dichloromethane (3×)
  7. dry with materialthe organic layer dried over sodium sulfate
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-760e9a119e184c169cd0849c4ba276ae
出典データセット
uspto-grants-2013_07
特許番号
US08492554B2

反応ノート

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