Sodium Methoxide → Methyl 5-((2-propylpentyl)oxy)furan-2-carboxylate

HRID 63335Notes

Reaction equation

HRID 63335 reaction equation
[CH2:1]([CH:4]([CH2:23][CH2:24][CH3:25])[CH2:5][O:6][C:7]1[O:11][C:10]([C:12]([O:14][CH2:15]C(CCC)CCC)=[O:13])=[CH:9][CH:8]=1)[CH2:2][CH3:3].C[O-].[Na+]>CO>[CH2:23]([CH:4]([CH2:1][CH2:2][CH3:3])[CH2:5][O:6][C:7]1[O:11][C:10]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:8]=1)[CH2:24][CH3:25]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 866946392-Propylpentyl 5-((2-propylpentyl)oxy)furan-2-carboxylate

Product 1

HCID 86694638Methyl 5-((2-propylpentyl)oxy)furan-2-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Propylpentyl 5-((2-propylpentyl)oxy)furan-2-carboxylate (0.62 g, 1.76 mmol), NaOMe (30% in MeOH, 2 mL) in anhydrous MeOH (75 mL) were stirred at room temperature overnight then concentrated under reduced pressure. The residue was partitioned between aqueous NH4Cl (25%) and hexanes. Organic layer was washed with brine, dried over anhydrous MgSO4, concentrated under reduced pressure. Flash chromatography purification (5%-20% EtOAc—hexanes gradient) gave methyl 5-((2-propylpentyl)oxy)furan-2-carboxylate as a colorless oil. Yield (0.38 g, 85%); 1H NMR (400 MHz, CDCl3) δ 7.12 (d, J=4.0 Hz, 1H), 5.27 (d, J=3.5 Hz, 1H), 3.99 (d, J=5.9 Hz, 2H), 3.03 (s, 3H), 1.74-1.83 (m, 1H), 1.20-1.40 (8H), 0.86-0.94 (m, 6H).

Workup

  1. concentrationthen concentrated under reduced pressure
  2. customThe residue was partitioned between aqueous NH4Cl (25%) and hexanes
  3. washOrganic layer was washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customFlash chromatography purification (5%-20% EtOAc—hexanes gradient)

Sources & evidence

ORD record
ord-2f9fbe70aab541e383cc69fd81891f19
Source dataset
uspto-grants-2016_09
Patent number
US09447078B2

Reaction notes

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