Methyl iodide → (Z)-2-Bromo-3-methoxy-1-phenylundeca-1-en-4,10-diyne

HRID 1936917

반응식

HRID 1936917 반응식
[Br:1]/[C:2](/[CH:10]([OH:19])[C:11]#[C:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]#[CH:18])=[CH:3]\[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH-].[K+].[CH3:22]I>CS(C)=O>[Br:1]/[C:2](/[CH:10]([O:19][CH3:22])[C:11]#[C:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]#[CH:18])=[CH:3]\[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 11324570(Z)-2-Bromo-1-phenylundeca-1-en-4,10-diyn-3-ol

생성물 1

HCID 12052605(Z)-2-Bromo-3-methoxy-1-phenylundeca-1-en-4,10-diyne수율 68%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

To a solution of Compound 7 (303.0 mg, 0.96 mmol) and KOH (214.1 mg, 3.82 mmol) in DMSO (20 mL) was added MeI (271.3 mg, 1.91 mmol) followed by stirring at room temperature for 5 hours. The reaction was then quenched with saturated aqueous NH4Cl (20 mL) and extracted with EtOAc (50 mL×2). The combined organic layer was washed with brine, dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, 20 percent EtOAc in hexane) to give 214.3 mg (68 percent) of Compound 8: pale yellow oil; Rf=0.56 (20 percent EtOAc in hexane); IR (neat) 3296, 2940, 2232, 2116, 1446, 1078 cm−1; 1H NMR (300 MHz, CDCl3) δ7.68-7.65 (m, 2H), 7.38-7.25 (m, 3H), 7.29 (s, 1H), 4.76 (s, 1H), 3.42 (s, 3H), 2.36-2.31 (m, 2H), 2.26-2.21 (m, 2H), 1.95 (t, J=2.67 Hz, 1H), 1.74-1.65 (m, 4H); 13C NMR (75 MHz, CDCl3) δ135.4, 131.4, 129.8, 129.1, 128.8, 123.9, 89.2, 84.6, 77.5, 76.8, 69.3, 56.0, 28.1, 27.9, 19.0, 18.5; MS (+CI) m/z (relative intensity) 333 (M+H+, 81Br, 10), 331 (M+H+, 79Br, 12), 251 (100); HRMS (+EI) calcd for C18H19BrO 330.0619 (M+), found 330.0606.

후처리

  1. customThe reaction was then quenched with saturated aqueous NH4Cl (20 mL)
  2. extractionextracted with EtOAc (50 mL×2)
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash column chromatography (silica gel, 20 percent EtOAc in hexane)

출처 및 근거

ORD 기록
ord-a64cafc9a1b54542b6ca7854cb9fcd89
출처 데이터셋
uspto-grants-2002_05
특허 번호
US06391916B1

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