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

HRID 454447노트

반응식

HRID 454447 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-760e9a119e184c169cd0849c4ba276ae
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492554B2

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