Dichloromethane → 2-Acetoxy-4-[4-[3-(5-methyl-2-phenyl-4-oxazolyl)propionyl]phenyl]butyronitrile

HRID 977244

반응식

HRID 977244 반응식
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][C:15]([C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH:25]=[O:26])=[CH:19][CH:18]=1)=[O:16].[C-:27]#[N:28].[Na+].[C:30]([O:33]C(=O)C)(=O)[CH3:31].ClCCl>[Cl-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1.O>[C:30]([O:26][CH:25]([CH2:24][CH2:23][C:20]1[CH:19]=[CH:18][C:17]([C:15](=[O:16])[CH2:14][CH2:13][C:3]2[N:4]=[C:5]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[O:6][C:2]=2[CH3:1])=[CH:22][CH:21]=1)[C:27]#[N:28])(=[O:33])[CH3:31]

참가 물질

7

반응물 4

HCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 8929Sodium CyanideHCID 199656273-[4-[3-(5-Methyl-2-phenyl-4-oxazolyl)propionyl]phenyl]propionaldehyde

생성물 1

HCID 199656432-Acetoxy-4-[4-[3-(5-methyl-2-phenyl-4-oxazolyl)propionyl]phenyl]butyronitrile수율 99.3%

시약·촉매·용매 2

HCID 159952Benzyltributylammonium chloride촉매HCID 962Water용매

실험 절차

A mixture of 3-[4-[3-(5-methyl-2-phenyl-4-oxazolyl)propionyl]phenyl]propionaldehyde (1.47 g), sodium cyanide (0.25 g), acetic anhydride (0.52 g), benzyltributylammonium chloride [(C4H9)3 (C6H5CH2)N+Cl- ](0.66 g) and dichloromethane (30 ml)- water (10 ml) was stirred at room temperature for 18 hours. The organic layer was separated, washed with water, dried (MgSO4) and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography. From the fraction eluted with ethyl acetate-hexane (1:2), 2-acetoxy-4-[4-[3-(5-methyl- 2-phenyl-4-oxazolyl)propionyl]phenyl]butyronitrile (1.75 g, quantitative) was obtained as an oily substance. NMR (δ ppm in CDCl3): 2.13 (3H, s), 2.15-2.3 (2H, m), 2.38 (3H, s), 2.8-3.0 (4H, m), 3.39 (2H, t, J=7 Hz), 5.29 (1H, t, J=6.5 Hz), 7.28 (2H, d, J=8 Hz), 7.35-7.5 (3H, m), 7.9-8.05 (4H, m)

후처리

  1. customThe organic layer was separated
  2. washwashed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. washFrom the fraction eluted with ethyl acetate-hexane (1:2)

출처 및 근거

ORD 기록
ord-c8edab1bf1d841d89251980e8e93f5cf
출처 데이터셋
uspto-grants-1997_03
특허 번호
US05614544

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