Tetrahydrofuran → 9-Heptadecanone

HRID 976213

反応式

HRID 976213 の反応式
[CH2:1]([Mg]Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH2:11]1[CH2:15][O:14][CH2:13][CH2:12]1>>[CH2:1]([C:13]([CH2:12][CH2:11][CH2:15][CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])=[O:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

参加物

3

反応物 2

HCID 8028Tetrahydrofuran2 回HCID 178443577HCID 178443577、化合物

生成物 1

HCID 108879-Heptadecanone収率 88%

実験手順

To a solution of 4.0 g (14.5 mmol) of the LIVb in 100 mL of THF was added 20 mL (40 mmol) of 2M octylmagnesium bromide in THF dropwise. After stirring 3.5 h, the solution was quenched with saturated NH4Cl, acidified with 1N HCl, and was extracted with EtOAc. The combined organic layers were washed with brine and dried over MgSO4. The solvent was removed under reduced pressure and the residue was chromatographed on silica gel. Elution with 7.5% ethyl acetate in hexanes gave 4.86 g (88%) of the bis-octyl ketone LIVc as an oil. 1H NMR (300 MHz, CDCl3) δ 4.55 (s, 2H, CH), 2.64 (dt, 4H, CH2), 1.62 (m, 4H, CH2), 1.42 (s, 6H, CH3), 1.27 (broad s, 20H, CH2), 0.88 (t, 6H, CH3); MS (CI,NH3) m/e 383 (M+1).

後処理

  1. customthe solution was quenched with saturated NH4Cl
  2. extractionwas extracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was chromatographed on silica gel
  7. washElution with 7.5% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-af5239da43a9470fb3e512cc41d0a289
出典データセット
uspto-grants-1997_03
特許番号
US05610294

関連ノート

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