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

HRID 2083308노트

반응식

HRID 2083308 반응식
[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

참가 물질

9

반응물 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 213175735-(4-Fluorophenoxy)-1-penten-4-olHCID 178418361HCID 178418361, 화합물

생성물 1

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

시약·촉매·용매 4

HCID 887Methanol촉매HCID 962Water용매HCID 6228Dimethylformamide용매3회HCID 8058Hexane용매

실험 절차

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)δ2.37 (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).

후처리

  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

출처 및 근거

ORD 기록
ord-af4e144183e94ff09f3bd4dd38f58f71
출처 데이터셋
uspto-grants-1978_04
특허 번호
US04085125

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