Ethylene Glycol → Methyl 5-(2-methyl-1,3-dioxolan-2-yl)pentanoate

HRID 1189356Notes

Reaction equation

HRID 1189356 reaction equation
N#N.[CH3:3][O:4][C:5](=[O:13])[CH2:6][CH2:7][CH2:8][CH2:9][C:10](=[O:12])[CH3:11].COC(OC)OC.[CH2:21](O)[CH2:22][OH:23]>>[CH3:3][O:4][C:5](=[O:13])[CH2:6][CH2:7][CH2:8][CH2:9][C:10]1([CH3:11])[O:23][CH2:22][CH2:21][O:12]1

Participants

5

Reactant 4

HCID 174Ethylene GlycolHCID 947NitrogenHCID 9005Trimethyl orthoformateHCID 288022Heptanoic acid, 6-oxo-, methyl ester

Product 1

HCID 11063488Methyl 5-(2-methyl-1,3-dioxolan-2-yl)pentanoate

Conditions

Temperature
95 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 6-oxo-heptanoic acid methyl ester (7.96 g, 50.32 mmol) in ethylene glycol (55.0 mL) was treated with trimethylorthoformate (10.65 mL, 110.14 mmol) followed by LiBF4 (963 mg, 10.06 mmol). The reaction mixture was heated at 95° C. for 14 h. The reaction mixture was cooled to rt and partitioned between EA and sat. aq. NaHCO3 The layers were separated and the aq. layer extracted with EA. The combined org. extracts were washed with sat. aq. NaHCO3, dried over Na2SO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (50:1→2:1 hept-EA) gave the title compound as a dark yellow oil. TLC: rf (3:1 hept-EA)=0.30.

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. custompartitioned between EA and sat. aq. NaHCO3 The layers
  3. customwere separated
  4. extractionthe aq. layer extracted with EA
  5. washextracts were washed with sat. aq. NaHCO3
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customthe solvent was removed under reduced pressure
  9. customPurification of the residue by FC (50:1→2:1 hept-EA)

Sources & evidence

ORD record
ord-67c7522449bf47aa8e2c5bc01e358a90
Source dataset
uspto-grants-2014_03
Patent number
US08674111B2

Reaction notes

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