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

HRID 81040ノート

反応式

HRID 81040 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-437a03cf09474dd38450ff67c54fac39
出典データセット
uspto-grants-2014_09
特許番号
US08846673B2

反応ノート

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