Allyl bromide → HCID 66705960, 화합물

HRID 2276377

반응식

HRID 2276377 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 66705960HCID 66705960, 화합물수율 80%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-74ccacda75ef4b36acfee4bf7b142e12
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09132136B2

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