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

HRID 1503634노트

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HRID 1503634 반응식
[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]

참가 물질

6

반응물 4

HCID 702EthanolHCID 7748Ethyl bromoacetateHCID 8467EthylvanillinHCID 11430Potassium Carbonate

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-58523edf728746dbb1caec96a52ac10c
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09212196B2

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