Boron trifluoride etherate → Methyl 2-methyl-1,3-dithiolane-2-propanoate

HRID 235690

Reaction equation

HRID 235690 reaction equation
[C:1]([O:8][CH3:9])(=[O:7])[CH2:2][CH2:3]C(C)=O.[CH:10]([SH:13])([SH:12])[CH3:11].B(F)(F)F.[CH3:18][CH2:19]OCC>CO>[CH3:11][C:10]1([CH2:3][CH2:2][C:1]([O:8][CH3:9])=[O:7])[S:13][CH2:19][CH2:18][S:12]1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherate2×HCID 336451,1-EthanedithiolHCID 69354Methyl levulinate

Product 1

HCID 10921676Methyl 2-methyl-1,3-dithiolane-2-propanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into a mixture of about 100 g of methyl levulinate and about 100 ml of ethanedithiol was slowly poured boron trifluoride etherate until reflux began. An about 500 ml portion of methanol was added followed by sufficient boron trifluoride etherate to make a total of about 100 ml of this reagent. The mixture was stirred overnight, the solvent removed and the residue poured into saturated sodium bi-carbonate. The mixture was extracted with ether. The ether extract was dried, the solvent removed and the residue distilled at about 97°-100° C., at about 0.55 mm, giving about 147 g of the desired title compound.

Workup

  1. temperatureuntil reflux
  2. customthe solvent removed
  3. additionthe residue poured into saturated sodium bi-carbonate
  4. extractionThe mixture was extracted with ether
  5. extractionThe ether extract
  6. customwas dried
  7. customthe solvent removed
  8. distillationthe residue distilled at about 97°-100° C., at about 0.55 mm

Sources & evidence

ORD record
ord-a6c17df02c8949b98cdcad08c60fd7ad
Source dataset
uspto-grants-1987_02
Patent number
US04640913

Linked notes

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