2,4-Hexadien-1-OL → 4,4'-Di-2,4-hexadienoxybenzophenone

HRID 611752노트

반응식

HRID 611752 반응식
F[C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11](F)=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].[CH2:19]([OH:25])[CH:20]=[CH:21][CH:22]=[CH:23][CH3:24]>CN(C=O)C>[CH2:19]([O:25][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:7][CH2:6][CH:5]=[CH:4][CH:3]=[CH:2][CH3:16])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1)[CH:20]=[CH:21][CH:22]=[CH:23][CH3:24]

참가 물질

5

반응물 3

HCID 81042,4-Hexadien-1-OLHCID 95824,4'-DifluorobenzophenoneHCID 24758Sodium hydride

생성물 1

HCID 538753704,4'-Di-2,4-hexadienoxybenzophenone수율 50.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

4,4'-Difluorobenzophenone (34) (4.8 grams, 22 mmol) was dissolved in anhydrous DMF (1 liter). NaH (95%; 5.6 grams, 220 mmol) was added and the solution was cooled to 0° C. 2,4-Hexadienol (5.8 mL, 51 mmol) was slowly added to the solution and the reaction mixture was allowed to warm to room temperature with stirring under argon overnight. The reaction mixture was concentrated in vacuo, dissolved in dichloromethane, and washed with water. The organic phase was dried (MgSO4) and concentrated and purified by column chromatography (silica gel; hexane/CH2Cl2, 1/3) to afford 2.07 grams (25%) of compound 35 as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 1.73 (d, J=6.6 Hz, 6H), 4.68 (d, J=6.0 Hz, 4H), 5.69-5.84 (m, 4H), 6.05-6.19 (m, 2H), 6.31-6.45 (m, 2H), 7.08 (d, J=9.0 Hz, 4), 7.68 (d, J=10.2 Hz, 4).

후처리

  1. temperatureto warm to room temperature
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutiondissolved in dichloromethane
  4. washwashed with water
  5. dry with materialThe organic phase was dried (MgSO4)
  6. concentrationconcentrated
  7. custompurified by column chromatography (silica gel; hexane/CH2Cl2, 1/3)

출처 및 근거

ORD 기록
ord-993632ae505c479aba1aa985bf9f4bdb
출처 데이터셋
uspto-grants-1999_12
특허 번호
US06001966

반응 노트

불러오는 중…