Benzyl Bromide → 4-Benzyloxy-5-(4-fluorophenoxy)-1-pentene

HRID 867096ノート

反応式

HRID 867096 の反応式
[F:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH2:7][CH:8]([OH:12])[CH2:9][CH:10]=[CH2:11])=[CH:4][CH:3]=1.CCCCCC.[H-].[Na+].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C)C=O>[CH2:23]([O:12][CH:8]([CH2:7][O:6][C:5]1[CH:13]=[CH:14][C:2]([F:1])=[CH:3][CH:4]=1)[CH2:9][CH:10]=[CH2:11])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

参加物

6

反応物 4

HCID 7498Benzyl BromideHCID 8058HexaneHCID 24758Sodium hydrideHCID 213175735-(4-Fluorophenoxy)-1-penten-4-ol

生成物 1

HCID 213176584-Benzyloxy-5-(4-fluorophenoxy)-1-pentene

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒3 回

反応条件

温度
25 °C

実験手順

A solution of 5-(4-fluorophenoxy)-1-penten-4-ol (9.81 g., 0.05 mole) in dry dimethylformamide (15 ml.) is added dropwise to a stirred suspension of hexane (2 × 10 ml.)--prewashed sodium hydride (50% dispersion in mineral oil, 2.64 g., 0.055 mole) in dry dimethylformamide (45 ml.) at 25° C. Upon cessation of gas evolution, the reaction mixture is cooled to 0°-5° C. and treated with a solution of benzyl bromide (10.3 g., 0.06 mole) in dry dimethylformamide (10 ml.). The resulting mixture is stirred at 25° C. for 16 hours, then heated at 100° C. for 1 hour. After cooling to 25° C., the reaction mixture is diluted with ice water (50 ml.) and extracted with ether four times. The combined organic extract is washed with 2 N hydrochloric acid and saturated aqueous brine, dried over magnesium sulfate and filtered. In vacuo evaporation of the filtrate leaves an oily residue which affords the title compound upon distillation as a colorless oil (13.1 g., 92%), bp0.025 112°-116° C.; pmr (CCl4) δ2.37 (2H, t), 3.5-4.0 (3H, m), 4.57 (2H, s), 4.8-5.05 (H, m), 5.05-5.25 (H, m), 5.4-6.2 (H, m), 6.6-7.1 (4H, m) and 7.19 (5H, s).

後処理

  1. customat 25° C
  2. temperatureUpon cessation of gas evolution, the reaction mixture is cooled to 0°-5° C.
  3. temperatureheated at 100° C. for 1 hour
  4. temperatureAfter cooling to 25° C.
  5. extractionextracted with ether four times
  6. extractionThe combined organic extract
  7. washis washed with 2 N hydrochloric acid and saturated aqueous brine
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customIn vacuo evaporation of the filtrate
  11. customleaves an oily residue which

出典と根拠

ORDレコード
ord-2b9ed2ca36b14e29a8b280b667b0512f
出典データセット
uspto-grants-1978_07
特許番号
US04102888

反応ノート

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