Dimethyl Sulfoxide → HCID 14456778, compound

HRID 1032036Notes

Reaction equation

HRID 1032036 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH:12]([CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].C(N(CC)CC)C>ClCCl>[O:11]=[C:12]([CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 15097815HCID 15097815, compound

Product 1

HCID 14456778HCID 14456778, compoundYield 63.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-70 °C

Procedure

To a solution of 0.39 ml of oxalyl chloride in 12 ml of dichloromethane was added under nitrogen atmosphere at -70° C. while stirring a solution of 0.60 ml of dimethyl sulfoxide in 4 ml of dichloromethane. To the mixture was added a solution of 0.95 g of 1-t-butyl 5-methyl 2-hydoxyglutarate obtained as above in 3.5 ml of dichloromethane. The whole mixture was stirred for 15 minutes at -70° C., to which was added 3.0 ml of triethylamine. The temperature of the reaction mixture was raised to -40° C., and the reaction mixture was poured into ice-water, followed by extraction with dichloromethane. The extract was wahsed with water, dilute acetic acid and water, in sequence, which was then dried (Na2SO4.), followed by distilling off the solvent. The residue was subjected to a silica gel column chromatography, eluting with hexane-ethyl acetate (5:1), followed by combining fractions containing the end product. Thus combined eluate was concentrated under reduced pressure to give 0.60 g of 1-t-butyl 5-methyl 2-oxoglutarate as a colorless oily substance.

Workup

  1. temperatureThe temperature of the reaction mixture was raised to -40° C.
  2. extractionfollowed by extraction with dichloromethane
  3. dry with materialwas then dried (Na2SO4.)
  4. distillationby distilling off the solvent
  5. washeluting with hexane-ethyl acetate (5:1)
  6. additioncontaining the end product
  7. concentrationThus combined eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-fced9be0ab3042a3bc5cef947e16f143
Source dataset
uspto-grants-1990_09
Patent number
US04956358

Reaction notes

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