Tetrahydrofuran → Methyl Benzoate

HRID 218988Notes

Reaction equation

HRID 218988 reaction equation
CCCCCC[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].C[O-:15].[Na+].[H][H].C1[CH2:23][O:22]CC1>>[C:13]([O:22][CH3:23])(=[O:15])[C:12]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran5×HCID 12388TridecaneHCID 10942334Sodium MethoxideHCID 178418361HCID 178418361, compound

Product 1

HCID 7150Methyl Benzoate

Procedure

Under argon, a Keim autoclave was charged with [RuCl2(R-BINAP)(dmf)2] (0.01 mmol, 0.05 mol %) and S,S-DPEN (0.01 mmol, 0.05 mol %) followed by THF (2 ml) and the solution stirred for 5 minutes. Then a solution of the desired ester (20 mmol) in THF (2 ml), followed by more THF (2×1 ml), and a solution of tridecane (1 mmol) in THF (2 ml), as internal standard, followed by more THF (2×1 ml), were successively added to the autoclave. Finally, solid NaOMe (1 mmol, 5 mol %) was added and the autoclave was pressurised with hydrogen gas at 50 bars and placed in a thermostatted oil bath set at 60° C. After the mentioned time, the autoclave was removed from the oil bath, and cooled in a cold-water bath. Then, an aliquot (0.4 ml) was taken, diluted with MTBE (5 ml), washed with aq. sat. NH4Cl (5 ml), and filtered over a plug of celite and analyzed by GC.

Workup

  1. additionwere successively added to the autoclave
  2. customplaced in a thermostatted oil bath
  3. customset at 60° C
  4. customAfter the mentioned time, the autoclave was removed from the oil bath
  5. temperaturecooled in a cold-water bath
  6. additiondiluted with MTBE (5 ml)
  7. washwashed with aq. sat. NH4Cl (5 ml)
  8. filtrationfiltered over a plug of celite

Sources & evidence

ORD record
ord-53a632ec64be421eab113ca94feb7245
Source dataset
uspto-grants-2012_06
Patent number
US08198488B2

Reaction notes

Loading…