Allyl bromide → 6-Allyloxy-4-ethyl-3-methyl-phthalic Acid Dimethyl Ester

HRID 2114242노트

반응식

HRID 2114242 반응식
[CH3:1][O:2][C:3](=[O:18])[C:4]1[C:5](=[C:10]([CH3:17])[C:11]([CH2:15][CH3:16])=[CH:12][C:13]=1[OH:14])[C:6]([O:8][CH3:9])=[O:7].C(=O)([O-])[O-].[K+].[K+].[CH2:25](Br)[CH:26]=[CH2:27]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:18])[C:4]1[C:5](=[C:10]([CH3:17])[C:11]([CH2:15][CH3:16])=[CH:12][C:13]=1[O:14][CH2:27][CH:26]=[CH2:25])[C:6]([O:8][CH3:9])=[O:7]

참가 물질

5

반응물 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 597944774-Ethyl-6-hydroxy-3-methyl-phthalic Acid Dimethyl Ester

생성물 1

HCID 574598616-Allyloxy-4-ethyl-3-methyl-phthalic Acid Dimethyl Ester수율 83.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

4-Ethyl-6-hydroxy-3-methyl-phthalic acid dimethyl ester (1.01 g, 4.02 mmol) was dissolved in DMF (5 mL). Potassium carbonate (3.33 g, 24.14 mmol) was added, followed by allylbromide (2.92 g, 24.14 mmol). The suspension was heated at 60° C. After 14 hours, the reaction was cooled to room temperature and filtered. The solvents were removed in vacuo and the crude material was purified by silica gel chromatography to provide 0.976 g (83%) of the desired product as a colorless oil. 1H NMR (300 MHz, CDCl3): δ=1.16 (t, J=7.2 Hz, 3H), 2.20 (s, 3H), 2.62 (q, J=7.2 Hz, 2H), 3.83 (s, 3H), 3.84 (s, 3H), 4.57 (m, 2H), 5.26 (dd, J=9.3, 1.5 Hz, 1H), 5.41 (dd, J=13.5, 1.5 Hz, 1H), 5.98 (m, 1H), 6.82 (s, 1H) ppm.

후처리

  1. temperaturethe reaction was cooled to room temperature
  2. filtrationfiltered
  3. customThe solvents were removed in vacuo
  4. customthe crude material was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-2964598c0133455aa2810cec86b03e77
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07432261B2

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