Sodium hydride → (S)-4-Bromo-3-(pent-4-en-2-yloxy)benzonitrile

HRID 1400748노트

반응식

HRID 1400748 반응식
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1F.[CH3:11][C@H:12]([OH:16])[CH2:13][CH:14]=[CH2:15].[H-].[Na+]>C1COCC1.CCOCC>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[O:16][C@H:12]([CH2:13][CH:14]=[CH2:15])[CH3:11]

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 6994332(S)-(+)-4-Penten-2-olHCID 151654434-Bromo-3-fluorobenzonitrile

생성물 1

HCID 86710808(S)-4-Bromo-3-(pent-4-en-2-yloxy)benzonitrile수율 71%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 4-bromo-3-fluorobenzonitrile (1.0 g, 5.00 mmol, 1 equiv) and (S)-pent-4-en-2-ol (0.52 g, 6.00 mmol, 1.2 equiv) in THF (25 mL) was added NaH (0.24 g of a 60% suspension in mineral oil, 6.00 mmol, 1.2 equiv). Slow gas evolution with considerable foaming observed. After 5 h, dilute with ether then wash with water and brine. The ether layer was dried (MgSO4) and concentrated in vacuo. The crude product was purified by flash column chromatography (0-10% EtOAc in hexane) to provide the product as a colorless oil (0.94 g, 71%). 1H NMR (400 MHz, CDCl3) δ 7.69-7.62 (m, 1H), 7.15-7.08 (m, 2H), 5.89 (ddt, J=17.1, 10.1, 7.2 Hz, 1H), 5.23-5.12 (m, 2H), 4.54-4.42 (m, 1H), 2.61-2.51 (m, 1H), 2.51-2.40 (m, 1H), 1.39 (d, J=6.0 Hz, 3H).

후처리

  1. washthen wash with water and brine
  2. dry with materialThe ether layer was dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by flash column chromatography (0-10% EtOAc in hexane)

출처 및 근거

ORD 기록
ord-73f6fbee84994614a69fba8e2804418c
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08906929B2

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