Dimethyl Sulfoxide → 2-(5-Oxo-3-pentynyl)cyclopropanecarboxylic acid methyl ester

HRID 36812ノート

反応式

HRID 36812 の反応式
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][O:12][C:13]([CH:15]1[CH2:17][CH:16]1[CH2:18][CH2:19][C:20]#[C:21][CH2:22][OH:23])=[O:14].C(N(CC)CC)C.[Cl-].[Na+]>ClCCl>[CH3:11][O:12][C:13]([CH:15]1[CH2:17][CH:16]1[CH2:18][CH2:19][C:20]#[C:21][CH:22]=[O:23])=[O:14]

参加物

7

反応物 5

HCID 679Dimethyl SulfoxideHCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 542604932-(5-Hydroxy-3-pentynyl)cyclopropanecarboxylic acid methyl ester

生成物 1

HCID 571941542-(5-Oxo-3-pentynyl)cyclopropanecarboxylic acid methyl ester収率 97.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

反応条件

温度
-40 °C

実験手順

Oxalyl chloride (0.40 g, 3.1 mmol) was dissolved in dichloromethane, and the solution was cooled to -40° C. A solution of dimethyl sulfoxide (0.52 g, 6.2 mmol) in dichloromethane (2 ml) was added thereto over a period of 5 minutes, and the mixture was stirred for 20 minutes. A solution of 2-(5-hydroxy-3-pentynyl)cyclopropanecarboxylic acid methyl ester (0.37 g, 2 mmol) in dichloromethane (5 ml) was added thereto, and the mixture was stirred for 30 minutes. Then, triethylamine (1.7 ml, 12 mmol) was added thereto. The temperature was raised to 0° C., and a saturated sodium chloride aqueous solution was added thereto. The product was extracted with dichloromethane, dried over anhydrous magnesium sulfate and then purified by silica gel column chromatography to obtain the above identified compound (0.35 g, yield: 96%).

後処理

  1. stirringthe mixture was stirred for 30 minutes
  2. temperatureThe temperature was raised to 0° C.
  3. extractionThe product was extracted with dichloromethane
  4. dry with materialdried over anhydrous magnesium sulfate
  5. custompurified by silica gel column chromatography
  6. customto obtain the

出典と根拠

ORDレコード
ord-4396e180818a44a9afcb702bc14349a3
出典データセット
uspto-grants-1995_05
特許番号
US05416231

反応ノート

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