Trichloroacetyl chloride → Methyl 2-(2,2-dichloro-3-oxocyclobutyl)acetate

HRID 217243

반응식

HRID 217243 반응식
[CH3:1][O:2][C:3](=[O:7])[CH2:4][CH:5]=[CH2:6].[Cl:8][C:9]([Cl:14])(Cl)[C:10](Cl)=[O:11]>COCCOC.C(OCC)C.[Cu].[Zn]>[CH3:1][O:2][C:3](=[O:7])[CH2:4][CH:5]1[CH2:6][C:10](=[O:11])[C:9]1([Cl:14])[Cl:8]

참가 물질

6

반응물 2

HCID 6420Trichloroacetyl chlorideHCID 77314Methyl 3-butenoate

생성물 1

HCID 57686758Methyl 2-(2,2-dichloro-3-oxocyclobutyl)acetate수율 138.8%

시약·촉매·용매 3

HCID 10290809Zinc copper couple촉매HCID 3283Diethyl Ether용매HCID 80711,2-Dimethoxyethane용매

실험 절차

To a mixture of but-3-enoic acid methyl ester (1.00 g, 10 mmol) and zinc-copper couple (1.97 g) in 1,2-dimethoxyethane (4.89 ml) and diethyl ether (37 ml), trichloroacetyl chloride (2.98 ml, 26.7 mmol) is added at room temperature under nitrogen. The mixture is stirred at room temperature for 3 days. The mixture is filtrated and washed with diethyl ether. The filtrate is concentrated under reduced pressure, and the obtained residue is purified by silica gel column chromatography to give (2,2-dichloro-3-oxo-cyclobutyl)-acetic acid methyl ester (2.93 g, quant.); TLC (hexane/AcOEt, 3:1) Rf 0.35, 1H NMR (400 MHz, chloroform-d) δ ppm 2.68-2.74 (m, 1H), 2.94-3.00 (m, 1H), 3.06-3.13 (m, 1H), 3.33-3.41 (m, 1H), 3.51-3.57 (m, 1H), 3.75 (s, 3H).

후처리

  1. additionis added at room temperature under nitrogen
  2. filtrationThe mixture is filtrated
  3. washwashed with diethyl ether
  4. concentrationThe filtrate is concentrated under reduced pressure
  5. customthe obtained residue is purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-4b05ce4e2290473ba112f51b4a4d9e07
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193349B2

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