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

HRID 328792ノート

反応式

HRID 328792 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.[H-].[Na+].[H][H].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C)C=O.CO.O.CCCCCC>[CH2:19]([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:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

参加物

9

反応物 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 213175735-(4-Fluorophenoxy)-1-penten-4-olHCID 178418361HCID 178418361、化合物

生成物 1

HCID 213176584-Benzyloxy-5-(4-fluorophenoxy)-1-pentene収率 92%

試薬・触媒・溶媒 4

HCID 887Methanol触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒3 回HCID 8058Hexane溶媒

実験手順

A solution of 5-(4-fluorophenoxy)-1-penten-4-ol (9.81 g., 50 mmoles) in dimethylformamide (15 ml.) is added dropwise to a suspension of hexane (2 × 10 ml.) prewashed sodium hydride (50% oil dispersion, 2.64 g., 55mmoles) in dimethylformamide (45 ml.). The resulting mixture is stirred until gas evolution ceases. (A few drops of methanol may be needed to initiate the evolution of hydrogen). The reaction mixture is chilled in an ice bath and treated with a solution of benzyl bromide (10.30 g., 60 mmoles) in dimethylformamide (10 ml.). The reaction mixture is then stirred at room temperature overnight (ca. 16 hours), and then heated on a steam bath for 1 hour. The reaction mixture is diluted with cold water (50 ml.), and extracted with ether four times. The combined extracts are washed with 2N hydrochloric acid and saturated brine and finally dried over anhydrous magnesium sulfate. After the removal of the solvent, the oil residue is vacuum distilled at 112°~6° C./0.025 mm. to give the title compound (13.1 g., 45.7 mmoles, 92%). ir (neat) 3.3~3.5, 6.08, 6.21, 6.65, 8.01, 8.28, 9.13, 10.90, 12.10, 13.18, 13.60, 14.40μ; pmr (CCl4)δ 2.37 (2H, t, J-5Hz), 3.5-4.0 (3H, m), 4.57 (2H, s), 4.8-5.05 (1H, m), 5.05-5.25 (1H, m), 5.4-6.2 (1H, m), 6.6-7.1 (4H, m), 7.19 (5H, s).

後処理

  1. temperatureThe reaction mixture is chilled in an ice bath
  2. stirringThe reaction mixture is then stirred at room temperature overnight (ca. 16 hours)
  3. temperatureheated on a steam bath for 1 hour
  4. extractionextracted with ether four times
  5. washThe combined extracts are washed with 2N hydrochloric acid and saturated brine
  6. dry with materialfinally dried over anhydrous magnesium sulfate
  7. customAfter the removal of the solvent
  8. distillationdistilled at 112°~6° C./0.025 mm

出典と根拠

ORDレコード
ord-229575318a9b47ae83ab0fb29b497969
出典データセット
uspto-grants-1977_04
特許番号
US04018802

反応ノート

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