Hydrochloric Acid → 2-(4-Benzyloxy-2,6-dichloro-benzyl)-2-(2,2-dimethoxy-ethyl)-malonic acid diethyl ester

HRID 1161767노트

반응식

HRID 1161767 반응식
[CH2:1]([O:3][C:4](=[O:17])[CH:5]([CH2:11][CH:12]([O:15][CH3:16])[O:13][CH3:14])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].[CH2:18]([O:25][C:26]1[CH:27]=[C:28]([Cl:35])[C:29]([CH2:33]Br)=[C:30]([Cl:32])[CH:31]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl>C1COCC1>[CH2:9]([O:8][C:6](=[O:7])[C:5]([CH2:33][C:29]1[C:28]([Cl:35])=[CH:27][C:26]([O:25][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:31][C:30]=1[Cl:32])([CH2:11][CH:12]([O:13][CH3:14])[O:15][CH3:16])[C:4]([O:3][CH2:1][CH3:2])=[O:17])[CH3:10]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 14215238Diethyl (2,2-dimethoxyethyl)malonateHCID 592994282-Bromomethyl-1,3-dichloro-5-benzyloxy-benzene

생성물 1

HCID 686483152-(4-Benzyloxy-2,6-dichloro-benzyl)-2-(2,2-dimethoxy-ethyl)-malonic acid diethyl ester수율 83.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Cool 2-(2,2-Dimethoxy-ethyl)-malonic acid diethyl ester (4.5 g, 16.3 mmol) in 50 mL THF to −78° C. and add lithium hexamethylsilane amide (1M, 17 mL) drop wise. After 15 min, add 5-benzyloxy-2-bromomethyl-1,3-dichloro-benzene (17.9 mmol 6.2 g) in 10 mL THF. Warm this mixture to ambient temperature, acidify with 1N HCl, and extract with ethyl acetate. Concentrate the organics and purify by normal phase column chromatography to afford the title compound as a white solid (7.0 g, 80%).

후처리

  1. extractionextract with ethyl acetate
  2. concentrationConcentrate the organics and
  3. custompurify by normal phase column chromatography

출처 및 근거

ORD 기록
ord-a666d68e49bb4753a72a92f0d2d38f37
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07820659B2

반응 노트

불러오는 중…