Water → HCID 66918669、化合物

HRID 1367479ノート

反応式

HRID 1367479 の反応式
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[SH:10].[CH:11]1(OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:15][CH:14]=[CH:13][CH2:12]1.O>CN(C=O)C>[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][CH:14]1[CH2:13][CH:12]=[CH:11][CH2:15]1

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 80599o-ChlorothiophenolHCID 357673HCID 357673、化合物

生成物 1

HCID 66918669HCID 66918669、化合物収率 79%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒3 回

反応条件

温度
0 °C

実験手順

NaH (316 mg, 55% in mineral oil, 7.24 mmol) was suspended in DMF (6 ml) and the suspension was cooled to 0° C. A solution of 2-chloro-thiophenol (880 ml, 97% purity, 7.55 mmol) in DMF (2 ml) was added dropwise. After stirring for 45 min at 0° C. a solution of toluene-4-sulfonic acid cyclopent-3-enyl ester (1500 mg, 6.29 mmol) in DMF (3 ml) was added dropwise and the reaction mixture was stirred at room temperature for 2 days. Water was added and the mixture was extracted 3 times with EtOAc. The combined organic layers were washed with water, saturated NaHCO3 solution and brine, dried over Na2OS4 and evaporated. The remaining brown oil was purified by silica gel chromatography (heptane/EtOAc 100:0-99:1) to obtain the title compound (1.047 g, 79%) as colorless liquid.

後処理

  1. additionwas added dropwise
  2. extractionthe mixture was extracted 3 times with EtOAc
  3. washThe combined organic layers were washed with water, saturated NaHCO3 solution and brine
  4. dry with materialdried over Na2OS4
  5. customevaporated
  6. customThe remaining brown oil was purified by silica gel chromatography (heptane/EtOAc 100:0-99:1)

出典と根拠

ORDレコード
ord-f2a008a51b2043f6a0f4796cddc43fce
出典データセット
uspto-grants-2011_02
特許番号
US07893099B2

反応ノート

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