Acetonitrile → (4E)-5-(3-Pyridyl)-4-penten-2-ol

HRID 489739

반응식

HRID 489739 반응식
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[CH3:8][CH:9]([OH:13])[CH2:10][CH:11]=[CH2:12].C(N(CC)CC)C.C(#N)C>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>[N:4]1[CH:5]=[CH:6][CH:7]=[C:2](/[CH:12]=[CH:11]/[CH2:10][CH:9]([OH:13])[CH3:8])[CH:3]=1

참가 물질

8

반응물 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 122474-Penten-2-OLHCID 122863-Bromopyridine

생성물 1

HCID 12042974(4E)-5-(3-Pyridyl)-4-penten-2-ol수율 96.8%

시약·촉매·용매 3

HCID 80271Tri-o-tolylphosphine촉매HCID 167845palladium(II) acetate촉매HCID 962Water용매

반응 조건

온도
140 °C

실험 절차

A mixture of 3-bromopyridine (7.50 g, 47.46 mmol), 4-penten-2-ol (4.90 g, 56.96 mmol), palladium(II) acetate (106 mg, 0.47 mmol), tri-o-tolylphosphine (575 mg, 1.89 mmol), triethylamine (28.4 mL, 204.11 mmol) and acetonitrile (25 mL) were heated in a sealed glass tube at 140° C. for 14 h. The reaction mixture was cooled to ambient temperature, diluted with water, and extracted with chloroform (3×200 mL). The combined chloroform extracts were dried over sodium sulfate, filtered, and concentrated by rotary evaporation to give a pale-yellow oil (7.50 g, 81.0%).

후처리

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. extractionextracted with chloroform (3×200 mL)
  3. dry with materialThe combined chloroform extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporation

출처 및 근거

ORD 기록
ord-feffb67306e446c1b0a403b902105424
출처 데이터셋
uspto-grants-2005_12
특허 번호
US06979695B2

연결된 노트

불러오는 중…