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

HRID 1966078ノート

反応式

HRID 1966078 の反応式
[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]>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]

参加物

5

反応物 2

HCID 6420Trichloroacetyl chlorideHCID 77314Methyl 3-butenoate

生成物 1

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

試薬・触媒・溶媒 2

HCID 10290809Zinc copper couple触媒HCID 3283Diethyl Ether溶媒

実験手順

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-dimethoxyothane (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).

後処理

  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

出典と根拠

ORDレコード
ord-6a86ec38893746ae9c670eb1a14379dc
出典データセット
uspto-grants-2013_04
特許番号
US08420641B2

反応ノート

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