Dimethyl Sulfoxide → HCID 85987067, compound

HRID 732636Notes

Reaction equation

HRID 732636 reaction equation
CS(C)=O.ClCCl.C(Cl)(=O)C(Cl)=O.[OH:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([CH3:26])([CH3:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21]>C(N(CC)CC)C>[CH3:26][C:19]([CH3:25])([CH2:18][CH2:17][CH2:16][CH:15]=[O:14])[C:20]([O:22][CH2:23][CH3:24])=[O:21]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6344Dichloromethane2×HCID 65578Oxalyl chlorideHCID 57424988HCID 57424988, compound

Product 1

HCID 85987067HCID 85987067, compoundYield 108.6%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A 4.0 ml portion of DMSO was added at −78° C. to a 40 ml dichloromethane solution of 2.5 ml oxalyl chloride and stirred for 10 minutes, and then a dichloromethane solution of 2.7 g of ethyl 6-hydroxy-2,2-dimethylhexanoate synthesized by the technique described in “Tetrahedron”, 2000, vol. 56, p. 9195-9202, was added thereto and stirred at the same temperature for 15 minutes. A 12 ml portion of triethylamine was added to the reaction solution and stirred for 30 minutes, and the reaction was quenched by adding water. Successively, work-up was carried out in the standard method to obtain 2.9 g of ethyl 2,2-dimethyl-6-oxohexanoate as a crude product. EP: 187.

Workup

  1. addition9195-9202, was added
  2. stirringstirred at the same temperature for 15 minutes
  3. stirringstirred for 30 minutes
  4. customthe reaction was quenched
  5. additionby adding water

Sources & evidence

ORD record
ord-b0f640add3df4399b85005afa1223de8
Source dataset
uspto-grants-2009_09
Patent number
US07585886B2

Reaction notes

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