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

HRID 1449849노트

반응식

HRID 1449849 반응식
C1(C)C=CC=CC=1.[F:8][CH:9](F)[C:10](C(O)=O)([CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)[C:11](OCC)=[O:12].[OH-].[Na+]>O>[F:8]/[CH:9]=[C:10](\[CH2:16][CH2:17][C:18]1[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=1)/[CH2:11][OH:12]

참가 물질

5

반응물 3

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 15342052Ethyl 2-(difluoromethyl)-2-carboxy-4-(p-fluorophenyl)butyrate

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
25 °C

실험 절차

Cool to 0° C.-10° C. a toluene solution of ethyl 2-(difluoromethyl)-2-carboxy-4-(p-fluorophenyl)butyrate as prepared in Example 4.1. Add water (396 kg) and a 50% by weight aqueous solution of sodium hydroxide. Stir for 30 minutes. Separate the aqueous layer and cool the aqueous layer to 0° C.-5° C. Add tetrahydrofuran (421 kg). Stir for hour at 0° C. and then warm to 25° C. and stir for 3 hours. Separate the aqueous layer. Evaporate the organic layer in vacuo at a temperature of 40° C.-50° C. The evaporation is continued until tetrahydrofuran no longer comes over and then toluene is added. Evaporate in vacuo until there is no longer water visible in the condensate. Concentrate in vacuo to give the title compound as a 80-90% by weight solution in toluene. An analytical sample prepared by evaporation of solvent gave 1H NMR (CDCl3, 300 MHz) δ 1.28 (t, J=7.2Hz 3H), 2.58 (m, 2H), 2.71 (m, 2H) 4.21 (q, J=7.2Hz, 2H), 6.93 (m, 2H), 7.15 (m, 2H), 7.51 (d, J=81.9Hz, 1H).

후처리

  1. customas prepared in Example 4.1
  2. customSeparate the aqueous layer
  3. temperaturecool the aqueous layer to 0° C.-5° C
  4. stirringStir for hour at 0° C.
  5. stirringstir for 3 hours
  6. customSeparate the aqueous layer
  7. customEvaporate the organic layer in vacuo at a temperature of 40° C.-50° C
  8. customThe evaporation
  9. additionis added
  10. customEvaporate in vacuo until there
  11. concentrationConcentrate in vacuo

출처 및 근거

ORD 기록
ord-2cd2bed384e345ce8af041ac69d9da14
출처 데이터셋
uspto-grants-1997_02
특허 번호
US05599986

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