Ethanol → Ethyl 2-(2-ethoxy-4-formylphenoxy)acetate

HRID 1503634ノート

反応式

HRID 1503634 の反応式
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[OH:12])[CH:7]=[O:8])[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH2:19]([O:21][C:22](=[O:25])[CH2:23]Br)[CH3:20].C(O)C>CC(C)=O>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:7]=[O:8])[CH:9]=[CH:10][C:11]=1[O:12][CH2:23][C:22]([O:21][CH2:19][CH3:20])=[O:25])[CH3:2]

参加物

6

反応物 4

HCID 702EthanolHCID 7748Ethyl bromoacetateHCID 8467EthylvanillinHCID 11430Potassium Carbonate

生成物 1

HCID 880082Ethyl 2-(2-ethoxy-4-formylphenoxy)acetate収率 63.6%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

The compound was prepared according to general procedure E with 3-ethoxy-4-hydroxybenzaldehyde (2.4 mmol) in dry acetone (15 ml), anhydrous K2CO3 (3.1 mmol), and ethylbromoacetate (3.6 mmol) at reflux for 1 h30. Ethanol was added and evaporated by azeotropic distillation with ethylbromoacetate. 565 mg of crude product were obtained and purified by silica gel chromatography (eluent dichloromethane). 385 mg of purified compound were obtained (63% yield). 1H NMR (250 MHz, CDCl3): δ 1.31 (t, J=7.0 Hz, 3H), 1.49 (t, J=7.0 Hz, 3H), 4.18 (q, J=7.0 Hz, 2H), 4.31 (q, J=7.0 Hz, 2H), 4.79 (s, 2H), 6.91 (d, J=8.0 Hz, 1H), 7.42 (d, J=8.0 Hz, 1H), 7.45 (s, 1H) 9.86 (s, 1H) 13C NMR (63 MHz, CDCl3): δ 14.0, 14.5, 61.2, 64.4, 65.9, 111.2, 113.0, 125.5, 131.0, 149.1, 152.7, 168.1, 191.5. MS (ESI): m/z 253.0 [M+H]+.

後処理

  1. customThe compound was prepared
  2. temperatureat reflux for 1 h30
  3. customevaporated by azeotropic distillation with ethylbromoacetate
  4. custom565 mg of crude product were obtained
  5. custompurified by silica gel chromatography (eluent dichloromethane)

出典と根拠

ORDレコード
ord-58523edf728746dbb1caec96a52ac10c
出典データセット
uspto-grants-2015_12
特許番号
US09212196B2

反応ノート

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