Benzaldehyde → (Benzylamino)acetaldehyde diethyl acetal

HRID 576864노트

반응식

HRID 576864 반응식
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9]([O:11][CH:12]([O:15][CH2:16][CH3:17])[CH2:13][NH2:14])[CH3:10].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C>O1CCCC1.C(OCC)(=O)C>[CH2:1]([NH:14][CH2:13][CH:12]([O:15][CH2:16][CH3:17])[O:11][CH2:9][CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 240BenzaldehydeHCID 695242,2-DiethoxyethylamineHCID 2724942Triacetoxyborohydride

생성물 1

HCID 521961(Benzylamino)acetaldehyde diethyl acetal수율 70%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of benzaldehyde 5.1 ml (50.0 mmol) in 2,2-diethoxyethanamine 10.9 ml (75.0 mmol) was stirred at room temperature for 0.5 hour. The reaction mixture was diluted with tetrahydrofuran 450 ml and triacetoxyborohydride 32.0 g (150 mmol) was added and the mixture was stirred overnight. The reaction mixture was diluted with ethyl acetate 500 ml and washed with saturated sodium bicarbonate 500 ml, water 500 ml and brine 500 ml. The organic phase was dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was purified on silica gel column chromatography (n-hexane:ethyl acetate=70:30 to 50:50) to obtain the title compound 7.8 g (yield 70%).

후처리

  1. additionwas added
  2. washwashed with saturated sodium bicarbonate 500 ml, water 500 ml and brine 500 ml
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was purified on silica gel column chromatography (n-hexane:ethyl acetate=70:30 to 50:50)

출처 및 근거

ORD 기록
ord-1952e2c14c2e4932a9a22d8ce7bacc9c
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040531B2

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