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

HRID 1449850노트

반응식

HRID 1449850 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

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온도
-15 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ee1314f67af346aa9e894523bf9aa29b
출처 데이터셋
uspto-grants-1997_02
특허 번호
US05599986

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