Water → 4-(2,2-Diethoxyethoxy)benzonitrile

HRID 2219192노트

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HRID 2219192 반응식
C(=O)([O-])[O-].[K+].[K+].[C:7]([C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)#[N:8].[CH2:16]([O:18][CH:19]([O:22][CH2:23][CH3:24])[CH2:20]Br)[CH3:17].O>CN(C=O)C.CCOC(C)=O>[CH2:16]([O:18][CH:19]([O:22][CH2:23][CH3:24])[CH2:20][O:15][C:12]1[CH:13]=[CH:14][C:9]([C:7]#[N:8])=[CH:10][CH:11]=1)[CH3:17]

참가 물질

7

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 130194-CyanophenolHCID 74852Ethane, 2-bromo-1,1-diethoxy-

생성물 1

HCID 177499644-(2,2-Diethoxyethoxy)benzonitrile수율 71%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

Powdered potassium carbonate (5.18 g, 37.7 mmol) is added to a stirred solution of 4-cyanophenol (2.00 g, 16.8 mmol) and bromoacetaldehyde diethyl acetal (4.53 mL, 30.3 mmol) in anhydrous DMF (20 mL). The resultant mixture is stirred at 85° C. under nitrogen for 3 days. The mixture is cooled to ambient temperature; then water (100 mL) and EtOAc (100 mL) are added to the mixture. The organic layer is separated, dried over MgSO4, filtered and concentrated. The oil is chromatographed on silica (gradient 5-20% EtOAc in hexane) to give 2.80 g (11.9 mmol, 71% yield) of the title compound. 1H NMR (CDCl3): δ1.24 (t, J=7.1 Hz, 6H), 3.60-3.68 (m, 2H), 3.73-3.81 (m, 2H), 4.04 (d, J=5.2 Hz, 2H), 4.83 (t, J=5.2 Hz, 1H), 6.97 (br d, J=9.2 Hz, 2H), 7.58 (br d, J=9.2 Hz, 2H); Analysis for C13H17NO3: calcd: C, 66.36; H, 7.28; N, 5.95; found: C, 66.41; H, 7.34; N, 6.01.

후처리

  1. customThe organic layer is separated
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe oil is chromatographed on silica (gradient 5-20% EtOAc in hexane)

출처 및 근거

ORD 기록
ord-9239dcce5db6453e891a05eb09984c25
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07414063B2

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