Tetrahydrofuran → 9-Heptadecanone

HRID 744989

반응식

HRID 744989 반응식
[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]

참가 물질

3

반응물 2

HCID 8028Tetrahydrofuran2회HCID 178443577HCID 178443577, 화합물

생성물 1

HCID 108879-Heptadecanone수율 88%

실험 절차

To a solution of the product of Example 1 (4.0 g, 14.5 mmol) in THF (100 mL) was added a solution of 2M octylmagnesium bromide in THF (20 mL, 40 mmol) dropwise. After stirring for 3.5 hr, 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 the bis-octyl ketone (III) (4.86 g, 88%) 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).

후처리

  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

출처 및 근거

ORD 기록
ord-0cd79e3cb3914dbc839782cbe8dcc619
출처 데이터셋
uspto-grants-1996_09
특허 번호
US05559252

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