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

HRID 1449849ノート

反応式

HRID 1449849 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
25 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-2cd2bed384e345ce8af041ac69d9da14
出典データセット
uspto-grants-1997_02
特許番号
US05599986

反応ノート

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