Sodium hydride → trans 2-Quinolin-6-yl-cyclopropanecarboxylic acid ethyl ester

HRID 655207

反応式

HRID 655207 の反応式
[H-].[Na+].[Cl-].[CH3:4][S+](C)(C)=O.[CH2:9]([O:11][C:12](=[O:25])[CH:13]=[CH:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]=[CH:20][CH:19]=[CH:18]2)[CH3:10]>CS(C)=O>[CH2:9]([O:11][C:12]([C@@H:13]1[CH2:4][C@H:14]1[C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]=[CH:20][CH:19]=[CH:18]2)=[O:25])[CH3:10]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 197819Trimethyloxosulphonium chlorideHCID 68531514HCID 68531514、化合物

生成物 1

HCID 86641540trans 2-Quinolin-6-yl-cyclopropanecarboxylic acid ethyl ester収率 59.3%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒2 回

実験手順

To a suspension of sodium hydride (71 mg, 1.76 mmol) in DMSO (3 mL) under nitrogen atmosphere was added trimethylsulfoxonium chloride (261 mg, 2.03 mmol). After stirring at room temperature for 30 minutes, a solution of 3-quinolin-6-yl-acrylic acid ethyl ester (200 mg, 0.881 mmol) in DMSO (2 mL) was added dropwise. The reaction mixture was stirred at room temperature for 2.5 h and quenched with a saturated aqueous solution of ammonium chloride. The mixture was extracted with ethyl acetate (2×) and the combined organic layers were washed with brine (3×) and adsorbed on silica gel. Purification on silica gel with 0-80% gradient of ethyl acetate in hexane provided 126 mg of product as a white solid. NMR 500 MHz (DMSO) δ 1.22 (t, 3H), 1.55 (m, 2H), 2.10 (m, 1H), 2.64 (m, 1H), 4.13 (q, 2H), 7.50 (dd, 1H), 7.58 (dd, 1H), 7.80 (d, 1H), 7.93 (d, 1H), 8.26 (dd, 1H), 8.84 (dd, 1H); MS (m/z) 242 [M+H+]+.

後処理

  1. stirringThe reaction mixture was stirred at room temperature for 2.5 h
  2. customquenched with a saturated aqueous solution of ammonium chloride
  3. extractionThe mixture was extracted with ethyl acetate (2×)
  4. washthe combined organic layers were washed with brine (3×)
  5. customPurification on silica gel with 0-80% gradient of ethyl acetate in hexane

出典と根拠

ORDレコード
ord-9dc7e8a11d014e5e835963c5cedf1807
出典データセット
uspto-grants-2011_12
特許番号
US08071581B2

関連ノート

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