4-Toluenesulfonyl chloride → Ethyl alpha-(4-methyl-phenylsulphonyloxymethylene)-phenylacetate

HRID 977935ノート

反応式

HRID 977935 の反応式
[OH:1][CH:2]=[C:3]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1>C(#N)C>[CH3:25][C:15]1[CH:20]=[CH:19][C:18]([S:21]([O:1][CH:2]=[C:3]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:4]([O:6][CH2:7][CH3:8])=[O:5])(=[O:23])=[O:22])=[CH:17][CH:16]=1

参加物

4

反応物 2

HCID 73974-Toluenesulfonyl chlorideHCID 70430766Ethyl 3-hydroxy-2-phenylprop-2-enoate

生成物 1

HCID 54306129Ethyl alpha-(4-methyl-phenylsulphonyloxymethylene)-phenylacetate収率 73%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

19.2 g (0.1 mol) of ethyl α-hydroxymethylene-phenylacetate are dissolved in 100 ml of acetonitrile, and first 11.2 g (0.1 mol) of potassium tert.-butylate are added, after which 19 g (0.1 mol) of p-toluenesulphonyl chloride are added in portions at 20° to 25° C. The mixture is stirred for 4 hours at room temperature and left to stand overnight. The precipitated salt is filtered off under suction, and the filtrate is evaporated down in vacuo. The residue is dissolved in toluene, and the solution is washed with water, dried over sodium sulphate and evaporated down in vacuo. 23 g (73% of theory) of ethyl α-(4-methyl-phenylsulphonyloxymethylene)-phenylacetate are obtained. The oil is dissolved in 150 ml of ethanol, and then 7.7 g (0.07 mol) of 2-hydrazino-pyrimidine are added. The mixture is stirred for 10 hours at room temperature, and then 13.5 g of concentrated sodium hydroxide solution are added dropwise in the course of 4 hours. After stirring has been continued for a further 5 hours at room temperature, dilute hydrochloric acid is added dropwise until the neutral point is reached, and the mixture is diluted with 750 ml of water. The oily product which separates out is taken up in a small amount of ether, 3.6 g (22% of theory) of 1-pyrimid-2-yl-4-phenylpyrazolin-5-one being precipitated. Melting point 159° to 160° C. (from ethanol).

後処理

  1. waitleft
  2. waitto stand overnight
  3. filtrationThe precipitated salt is filtered off under suction
  4. customthe filtrate is evaporated down in vacuo
  5. dissolutionThe residue is dissolved in toluene
  6. washthe solution is washed with water
  7. dry with materialdried over sodium sulphate
  8. customevaporated down in vacuo

出典と根拠

ORDレコード
ord-7bb0c0d5fd2e443ba6fd958f90c67f8d
出典データセット
uspto-grants-1987_05
特許番号
US04663327

反応ノート

読み込み中…