Dimethyl Sulfoxide → HCID 15037104, compound

HRID 1681514Notes

Reaction equation

HRID 1681514 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH2:11]([Si:13]([CH2:25][CH3:26])([CH2:23][CH3:24])[C:14]1[O:15][CH:16]=[C:17]([CH2:19][CH2:20][CH2:21][OH:22])[CH:18]=1)[CH3:12].C(N(CC)CC)C>ClCCl>[CH2:25]([Si:13]([CH2:11][CH3:12])([CH2:23][CH3:24])[C:14]1[O:15][CH:16]=[C:17]([CH2:19][CH2:20][CH:21]=[O:22])[CH:18]=1)[CH3:26]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 15037103HCID 15037103, compound

Product 1

HCID 15037104HCID 15037104, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of dimethyl sulfoxide (0.9 ml) and dichloromethane (9 ml) was added to a solution of oxalyl chloride (0.64 ml, 7.39 mmol) at -78 degrees under argon. After 5 minutes, a solution of 3-(2-triethylsilyl-4-furyl)propan-1-ol (1.27 g, 5.28 mmol) in dichloromethane (9.0 ml) was added dropwise and after 20 minutes, triethylamine (2.9 ml, 21.1 mmol) was added. Stirring was continued at -78 degrees C. for 40 minutes and at room temperature for 3 hours. The mixture was quenched with water and was extracted thoroughly with ethyl ether. Evaporation of the dried (magnesium sulfate) extracts gave an oil, which was purified by a silica column to give the titled aldehyde.

Workup

  1. customwas continued at -78 degrees C
  2. waitfor 40 minutes
  3. waitat room temperature for 3 hours
  4. customThe mixture was quenched with water
  5. extractionwas extracted thoroughly with ethyl ether
  6. customEvaporation of the
  7. dry with materialdried (magnesium sulfate)
  8. customextracts gave an oil, which
  9. customwas purified by a silica column

Sources & evidence

ORD record
ord-f43674d728af4e8cb18c910b041ae169
Source dataset
uspto-grants-1992_12
Patent number
US05171863

Reaction notes

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