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

HRID 1385480ノート

反応式

HRID 1385480 の反応式
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]

参加物

5

反応物 3

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

生成物 1

HCID 538753704,4'-Di-2,4-hexadienoxybenzophenone収率 50.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

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, ⅓) 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, 6 H), 4.68 (d, J=6.0 Hz, 4 H), 5.69-5.84 (m, 4 H), 6.05-6.19 (m, 2 H), 6.31-6.45 (m, 2 H), 7.08 (d, J=9.0 Hz, 4 H), 7.68 (d, J=10.2 Hz, 4 H).

後処理

  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, ⅓)

出典と根拠

ORDレコード
ord-c43e9170b87c48089b7c86b14202cbfe
出典データセット
uspto-grants-2001_07
特許番号
US06262251B1

反応ノート

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