Ethyl cyanoacetate → (E)-ethyl 2-cyano-3-(4-phenoxyphenyl)acrylate

HRID 81040노트

반응식

HRID 81040 반응식
P([O-])([O-])([O-])=O.[K+].[K+].[K+].[C:9]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])#[N:10].[O:17]([C:24]1[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(O)C>[C:9](/[C:11](=[CH:28]\[C:27]1[CH:30]=[CH:31][C:24]([O:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[CH:25][CH:26]=1)/[C:12]([O:14][CH2:15][CH3:16])=[O:13])#[N:10]

참가 물질

5

반응물 3

HCID 7764Ethyl cyanoacetateHCID 62657Potassium Phosphate, TribasicHCID 661394-Phenoxybenzaldehyde

생성물 1

HCID 86665688(E)-ethyl 2-cyano-3-(4-phenoxyphenyl)acrylate

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

Potassium phosphate (0.751 g, 3.54 mmol) was added to a solution of ethyl 2-cyanoacetate (2.00 g, 17.68 mmol) and 4-phenoxybenzaldehyde (3.50 g, 17.68 mmol) in ethanol (50 mL). After 1 h at room temperature, the mixture was quenched with water (20 mL). The ethanol solvent was evaporated in vacuo. The residue was taken up in ethyl acetate (150 mL), washed with brine (2×10 mL), dried (MgSO4) and concentrated. Silica gel chromatography, loading with toluene and eluting with 5 to 20% ethyl acetate in hexanes, gave (E)-ethyl 2-cyano-3-(4-phenoxyphenyl)acrylate as tan liquid. 1H NMR (500 MHz, CDCl3) δ ppm 8.19 (1H, s), 7.92-8.05 (2H, m), 7.37-7.48 (2H, m), 7.24 (1H, t, J=7.42 Hz), 7.10 (2H, δ, J=7.70 Hz), 6.98-7.07 (2H, m), 4.38 (2H, q, J=7.15 Hz), 1.40 (3H, δ, J=7.15 Hz); MS (ES+) m/z: 294 (M+H); LC retention time: 4.405 min (analytical HPLC Method B).

후처리

  1. customthe mixture was quenched with water (20 mL)
  2. customThe ethanol solvent was evaporated in vacuo
  3. washwashed with brine (2×10 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. washeluting with 5 to 20% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-437a03cf09474dd38450ff67c54fac39
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846673B2

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