Tetrahydrofuran → 9-Heptadecanone

HRID 2394378Notes

Reaction equation

HRID 2394378 reaction equation
[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]

Participants

3

Reactant 2

HCID 8028Tetrahydrofuran2×HCID 178443577HCID 178443577, compound

Product 1

HCID 108879-HeptadecanoneYield 88%

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-96ef666cf239442689d04b082390dcd3
Source dataset
uspto-grants-1998_09
Patent number
US05811422

Reaction notes

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