3-Phenylprop-2-En-1-Ol → (3-Phenyl-2-propene-1-yl) propiolate

HRID 890159ノート

反応式

HRID 890159 の反応式
[C:1]([OH:5])(=[O:4])[C:2]#[CH:3].[CH2:6](O)[CH:7]=[CH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C1(N=C=NC2CCCCC2)CCCCC1>CCOCC.CN(C)C1C=CN=CC=1>[C:1]([O:5][CH2:6][CH:7]=[CH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:4])[C:2]#[CH:3]

参加物

6

反応物 3

HCID 3083-Phenylprop-2-En-1-OlHCID 10110Propiolic AcidHCID 10868Dicyclohexylcarbodiimide

生成物 1

HCID 53746771(3-Phenyl-2-propene-1-yl) propiolate

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 3283Diethyl Ether溶媒2 回

反応条件

温度
-20 °C

実験手順

2.71 mg (44 mmol) of propiolic acid and 5.14 ml (40 mmol) of cinnamyl alcohol were dissolved in 20 ml of dry ether. The obtained solution was cooled to −20° C. 100 ml of a solution of 9.27 g (45 mmol) of dicyclohexylcarbodiimide and 0.36 g (30 mmol) of 4-dimethylaminopyridine in dry ether was dropped into the solution. The temperature of the obtained mixture was elevated to room temperature. After stirring overnight, the insoluble matter was filtered out. The filtrate was washed with 2 N hydrochloric acid and saturated aqueous salt solution, and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by the silica gel chromatography (hexane/ethyl acetate=10/1) to obtain the title compound.

後処理

  1. customwas elevated to room temperature
  2. filtrationthe insoluble matter was filtered out
  3. washThe filtrate was washed with 2 N hydrochloric acid and saturated aqueous salt solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by the silica gel chromatography (hexane/ethyl acetate=10/1)

出典と根拠

ORDレコード
ord-69d54832c1284664b6e37ad831945e7c
出典データセット
uspto-grants-2006_02
特許番号
US06995179B2

反応ノート

読み込み中…