Tetrahydrofuran → HCID 72698334, compound

HRID 1037020Notes

Reaction equation

HRID 1037020 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=O.[CH3:13][CH2:14][Mg+].[Br-].[CH2:17]1COC[CH2:18]1>>[Br:1][C:2]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:3]=1[C:4]([OH:6])([CH2:13][CH3:14])[CH2:17][CH3:18]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 21779704Methyl 2-bromo-4-methylbenzoateHCID 178461630HCID 178461630, compound

Product 1

HCID 72698334HCID 72698334, compoundYield 71.2%

Procedure

To a solution of methyl 2-bromo-4-methylbenzoate (10 g, 43.7 mmol) in THF (10 mL) was added dropwise EtMgBr (88 mL, 262 mmol) at 0° C. under nitrogen and then stirred at rt for 12 h. The reaction mixture was quenched with NH4Cl-saturated water and extracted with EA. The combined organic layer was washed with NaHCO3 solution and brine, dried over Na2SO4. The solution was concentrated and the residue was purified by column chromatography over silica gel eluted with PE-EA (10:1˜2:1) to provide 3-(2-bromo-4-methylphenyl)pentan-3-ol (8.09 g; yield 71.2%) as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.67 (d, 1 H), 7.52 (s, 1 H), 7.23 (d, 1 H), 2.35 (s, 3 H), 1.83 (m, 4 H), 0.77 (t, 6 H) ppm.

Workup

  1. customThe reaction mixture was quenched with NH4Cl-saturated water
  2. extractionextracted with EA
  3. washThe combined organic layer was washed with NaHCO3 solution and brine
  4. dry with materialdried over Na2SO4
  5. concentrationThe solution was concentrated
  6. customthe residue was purified by column chromatography over silica gel
  7. washeluted with PE-EA (10:1˜2:1)

Sources & evidence

ORD record
ord-8e0db85c5241448d9c2f95f8b1158e5b
Source dataset
uspto-grants-2013_10
Patent number
US08546357B2

Reaction notes

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