Dimethyl Sulfoxide → HCID 178469083, compound

HRID 1066578Notes

Reaction equation

HRID 1066578 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([SiH2:15][O:16][C:17]([CH3:32])([CH3:31])[C:18]1[CH:19]=[C:20]([CH:26]=[C:27]([CH2:29][OH:30])[CH:28]=1)[C:21]([O:23][CH2:24][CH3:25])=[O:22])([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C>C(Cl)Cl>[C:11]([SiH2:15][O:16][C:17]([CH3:31])([CH3:32])[C:18]1[CH:19]=[C:20]([CH:26]=[C:27]([CH:29]=[O:30])[CH:28]=1)[C:21]([O:23][CH2:24][CH3:25])=[O:22])([CH3:12])([CH3:13])[CH3:14]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 172695059HCID 172695059, compound

Product 1

HCID 178469083HCID 178469083, compoundYield 100.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.64 ml of oxalyl chloride was added at −60° C. to a solution of 0.76 ml of dimethyl sulphoxide in 10 ml of CH2Cl2. After 5 minutes 2 g of ethyl 3-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxymethyl-benzoate (Example 31.1) in 20 ml of CH2Cl2 were addded over 5 minutes in a manner such that the temperature did not exceed −60° C. After 15 minutes 4.295 m triethylamine were added. The reaction mixture was left too warm to room temperature and was worked up by extraction and yielded 2.0 g of ethyl 3-(tert-butyl-dimethyl-silanyloxymethyl)-5-formyl-benzoate.

Workup

  1. customdid not exceed −60° C
  2. waitThe reaction mixture was left too
  3. extractionwas worked up by extraction

Sources & evidence

ORD record
ord-b61e7f69e7444295b06506e544c0ddf3
Source dataset
uspto-grants-2001_06
Patent number
US06242644B1

Reaction notes

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