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

HRID 890159노트

반응식

HRID 890159 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 3283Diethyl Ether용매2회

반응 조건

온도
-20 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-69d54832c1284664b6e37ad831945e7c
출처 데이터셋
uspto-grants-2006_02
특허 번호
US06995179B2

반응 노트

불러오는 중…