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

HRID 1936917

反応式

HRID 1936917 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-a64cafc9a1b54542b6ca7854cb9fcd89
出典データセット
uspto-grants-2002_05
特許番号
US06391916B1

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