Hydrochloric Acid → (E)-2-(fluoromethylene)-4-(p-fluorophenyl)butan-1-ol

HRID 1449850ノート

反応式

HRID 1449850 の反応式
[F:1]/[CH:2]=[C:3](\[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)/[C:4](OCC)=[O:5].C1(C)C=CC=CC=1.[H-].C([Al+]CC(C)C)C(C)C.Cl>O.CO>[F:1]/[CH:2]=[C:3](\[CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=1)/[CH2:4][OH:5]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 15342053ethyl (E)-2-(fluoromethylene)-4-(p-fluorophenyl)butyrateHCID 21225700Diisobutylaluminumhydride

生成物 1

HCID 10943450(E)-2-(fluoromethylene)-4-(p-fluorophenyl)butan-1-ol

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
-15 °C

実験手順

Combine ethyl (E)-2-(fluoromethylene)-4-(p-fluorophenyl)butyrate (1.5 g, 6.24 mmol) and toluene (5 mL). Cool to -15° C. Add dropwise, a solution of diisobutylaluminum hydride (10.4 mL, 1.5M in toluene, 15.6 mmol). Warm to ambient temperature. After 18 hours, cool to 0° C. With vigorous stirring add sequentially, methanol (15 mL), an aqueous 5M hydrochloric acid solution (25 mL), and water (35 mL). When gas evolution ceases, extract with toluene. Separate the layers and evaporate organic layer in vacuo to give the title compound. 1H NMR (CDCl3, 300 MHz) δ 2.28 (s, 1H), 2.45 (m, 2H), 2.72 (m, 2H) 3.91 (d, J=3 Hz, 2H), 6.57 (d, J=87 Hz, 1H), 6.96 (m, 2H), 7.13 (m, 2H).

後処理

  1. additionAdd dropwise
  2. temperatureWarm to ambient temperature
  3. temperaturecool to 0° C
  4. additionadd sequentially
  5. extractionWhen gas evolution ceases, extract with toluene
  6. customSeparate the layers
  7. customevaporate organic layer in vacuo

出典と根拠

ORDレコード
ord-ee1314f67af346aa9e894523bf9aa29b
出典データセット
uspto-grants-1997_02
特許番号
US05599986

反応ノート

読み込み中…