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Water → 2,2-Dimethyl-3-(2-phenyl-vinyl)-cyclopropanecarboxylic acid ethyl ester

HRID 64920
ノート
印刷プレビュー

反応式

HRID 64920 の反応式
C(OP([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=O)OCC)C.C([Li])CCC.[CH2:21]([O:23][C:24]([CH:26]1[CH:28]([CH:29]=O)[C:27]1([CH3:32])[CH3:31])=[O:25])[CH3:22].O>O1CCCC1.CCCCCC>[CH2:21]([O:23][C:24]([CH:26]1[CH:28]([CH:29]=[CH:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:27]1([CH3:31])[CH3:32])=[O:25])[CH3:22]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 962WaterHCID 14122Diethyl benzylphosphonateHCID 566079Ethyl 3-formyl-2,2-dimethylcyclopropane-1-carboxylateHCID 178418339Butyllithium

生成物 1

HCID 544855342,2-Dimethyl-3-(2-phenyl-vinyl)-cyclopropanecarboxylic acid ethyl ester収率 69.6%

試薬・触媒・溶媒 2

HCID 8028
Tetrahydrofuran
溶媒
HCID 8058Hexane溶媒

反応条件

温度
-70 °C

実験手順

22.8 g (0.1 mol) of benzylphosphonic acid diethyl ester were dissolved in 400 ml of absolute tetrahydrofuran and the solution was cooled to -70° C. 0.11 mol of n-butyl-lithium (as a 15% strength solution in hexane) were added dropwise under a counter-current of nitrogen and while stirring well; the mixture was then stirred at -70° C. for a further 15 minutes, and thereafter 18.6 g (0.1 mol) of 2,2-dimethyl-3-formyl-cyclopropanecarboxylic acid ethyl ester were added dropwise at -65° C., again still under nitrogen. The reaction mixture was then allowed to come to room temperature and was stirred further for 3 hours at 25° C. Thereafter, the reaction batch was poured into 2 liters of water and extracted with 600 ml of ether. The ether phase was dried over sodium sulphate and the solvent was then stripped off in vacuo. The oily residue was distilled at 145°-150° C./3 mm Hg. 2,2 -Dimethyl-3-(2-phenyl-vinyl)-cyclopropanecarboxylic acid ethyl ester having a refractive index nD23 of 1.5022 was obtained in 69.6% yield.

後処理

  1. stirringthe mixture was then stirred at -70° C. for a further 15 minutes
  2. customto come to room temperature
  3. stirringwas stirred further for 3 hours at 25° C
  4. extractionextracted with 600 ml of ether
  5. dry with materialThe ether phase was dried over sodium sulphate
  6. distillationThe oily residue was distilled at 145°-150° C./3 mm Hg

出典と根拠

ORDレコード
ord-d51ec3015d224f0e8d1942f2149d546a
出典データセット
uspto-grants-1986_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04611009

反応ノート

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