Dimethyl Sulfoxide → Benzyl 2,2-dimethyl-5-oxopentanoate

HRID 1864817Notes

Reaction equation

HRID 1864817 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH2:12][CH2:13][CH2:14][C:15]([CH3:27])([CH3:26])[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17].C(N(CC)CC)C>C(Cl)Cl>[CH3:26][C:15]([CH3:27])([CH2:14][CH2:13][CH:12]=[O:11])[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 66972971Benzyl 5-hydroxy-2,2-dimethylpentanoate

Product 1

HCID 86616388Benzyl 2,2-dimethyl-5-oxopentanoateYield 91.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a −78° C. solution of oxalyl chloride (4.80 g, 37.8 mmol) in DCM (200 mL) was add DMSO (5.91 g, 75.6 mmol) dropwise over 10 minutes. After 25 minutes of additional stirring, a −78° C. solution of benzyl 5-hydroxy-2,2-dimethylpentanoate (4.06 g, 17.2 mmol, Step B) in DCM (200 mL) was added via cannula over 75 minutes. After stirring for an additional 30 minutes, triethylamine (13.9 g, 137 mmol) was added slowly over 25 minutes. The cooling bath was allowed to warm, while the reaction stirred for an additional 18 hours. Reaction solvent was then removed in vacuo, and the residue was dissolved in a mixture of diethyl ether and water (containing enough HCl to remain acidic). The organics were then dried over sodium sulfated, filtered and concentrated in vacuo to give the title compound (3.67 g), which was used without further purification.

Workup

  1. temperatureto warm, while the reaction
  2. stirringstirred for an additional 18 hours
  3. customReaction solvent
  4. customwas then removed in vacuo
  5. dissolutionthe residue was dissolved in a mixture of diethyl ether and water (containing enough HCl to remain acidic)
  6. dry with materialThe organics were then dried over sodium
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dcc79aa3bb04494b8c491afb6507ef74
Source dataset
uspto-grants-2009_12
Patent number
US07625901B2

Reaction notes

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