Allyl bromide → HCID 66705960、化合物

HRID 2276377

反応式

HRID 2276377 の反応式
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]([OH:12])[CH3:11])=[CH:6][CH:5]=1.[CH2:13](Br)[CH:14]=[CH2:15]>CN(C=O)C>[CH2:15]([O:12][C@H:10]([C:7]1[CH:8]=[CH:9][C:4]([F:3])=[CH:5][CH:6]=1)[CH3:11])[CH:14]=[CH2:13]

参加物

5

反応物 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 852997(-)-1-(4-Fluorophenyl)ethanol

生成物 1

HCID 66705960HCID 66705960、化合物収率 80%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a stirred suspension of sodium hydride (3.14 g, 55% dispersion in oil) in dry DMF (180 ml) under an argon atmosphere was added (S)-1-(4-fluorophenyl)-ethanol (8.41 g, CAS 101219-73-2). Allyl bromide (6.6 ml) was then added dropwise. The reaction mixture was stirred for 30 min at room temperature and was then quenched by addition of water. The mixture was extracted with ethyl acetate twice. The combined organic layers were dried (MgSO4) and concentrated in vacuo. The crude product was purified by column chromatography (SiO2; gradient: heptane/EtOAc) to give 1-((S)-1-allyloxy-ethyl)-4-fluoro-benzene (8.66 g, 80%) as a colourless liquid. 1H NMR (300 MHz, CDCl3, δ ppm): 1.43 (d, J=6.6 Hz, 3H), 3.84 (m, 2H), 4.45 (q, J=6.6 Hz, 1H), 5.15 (dd, J1=10.5 Hz, J2=1.8 Hz, 1H), 5.22 (dd, J1=17.4 Hz, J2=1.8 Hz, 1H), 5.89 (m, 1H), 7.03 (m, 2H), 7.29 (m, 2H).

後処理

  1. customwas then quenched by addition of water
  2. extractionThe mixture was extracted with ethyl acetate twice
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by column chromatography (SiO2; gradient: heptane/EtOAc)

出典と根拠

ORDレコード
ord-74ccacda75ef4b36acfee4bf7b142e12
出典データセット
uspto-grants-2015_09
特許番号
US09132136B2

関連ノート

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