1-Pentyne → Ethyl (3-(pentyne-1-yl)phenyl)acetate

HRID 59021

반응식

HRID 59021 반응식
[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8](Br)[CH:7]=1)[CH3:2].O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH:33]#[C:34][CH2:35][CH2:36][CH3:37]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[C:33]([C:8]1[CH:7]=[C:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:13])[CH:11]=[CH:10][CH:9]=1)#[C:34][CH2:35][CH2:36][CH3:37]

참가 물질

6

반응물 3

HCID 123091-PentyneHCID 11470552Ethyl 3-(bromophenyl)acetateHCID 162116731-Butanaminium, N,N,N-tributyl-, fluoride, hydrate

생성물 1

HCID 67100180Ethyl (3-(pentyne-1-yl)phenyl)acetate수율 80.5%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매

반응 조건

온도
80 °C

실험 절차

A mixture of ethyl(3-bromophenyl)acetate (0.3 g, 1.24 mmol) and tetrabutylammonium fluoride hydrate (0.97 g, 3.72 mmol), was treated with PdCl2(PPh3)2 (26 mg, 0.037 mmol; 3 mole %) and 1-pentyne (367 μL, 3.72 mmol) in a sealed tube. The tube was heated at 80° C. for 2 h. The mixture was treated with water, and was extracted with diethyl ether. The organic extract was dried over sodium sulfate, filtered and evaporated in vacuo to give the crude product. Purification on a Biotage™ 25 M column (silica), eluting with ethyl acetate/hexane 0:1 to 2:98, gave ethyl (3-(pentyne-1-yl)phenyl)acetate as a pale yellow oil (0.23 g, 79%).

후처리

  1. extractionwas extracted with diethyl ether
  2. extractionThe organic extract
  3. dry with materialwas dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto give the crude product
  7. customPurification on a Biotage™ 25 M column (silica)
  8. washeluting with ethyl acetate/hexane 0:1 to 2:98

출처 및 근거

ORD 기록
ord-88dbc1b4edb54ade9774a49832ce807e
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09439882B2

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