Dimethyl Sulfoxide → HCID 9819244, compound

HRID 1275625Notes

Reaction equation

HRID 1275625 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][C:12]1[C:13]([S:26][C:27]2[CH:32]=[CH:31][C:30]([CH2:33][OH:34])=[CH:29][CH:28]=2)=[CH:14][C:15]2[C:16]([CH3:25])([CH3:24])[CH2:17][CH2:18][C:19]([CH3:23])([CH3:22])[C:20]=2[CH:21]=1.C(N(CC)CC)C>ClCCl.O>[CH3:11][C:12]1[C:13]([S:26][C:27]2[CH:32]=[CH:31][C:30]([CH:33]=[O:34])=[CH:29][CH:28]=2)=[CH:14][C:15]2[C:16]([CH3:25])([CH3:24])[CH2:17][CH2:18][C:19]([CH3:22])([CH3:23])[C:20]=2[CH:21]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 9840907HCID 9840907, compound

Product 1

HCID 9819244HCID 9819244, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

60 μl (0.7 mmol) of oxalyl chloride and 5 ml of dichloromethane were introduced into a three-necked flask and under a nitrogen stream. 100 μl (1.4 mmol) of DMSO were added at -60° C. and the mixture was stirred for 10 min and then a solution of 200 mg (0.6 mmol) of 4-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthylthio)benzenemethanol in 5 ml of dichloromethane and 400 μl (3 mmol) of triethylamine was added. The mixture was stirred at room temperature for one hour, the reaction medium poured into water, extracted with dichloromethane, the organic phase decanted off, dried over magnesium sulfate and evaporated. The residue obtained was purified by chromatography on a silica column eluted with a mixture of heptane and ethyl acetate (80/20). 145 mg (73%) of the expected aldehyde of melting point 98-9° C. were recovered.

Workup

  1. stirringThe mixture was stirred at room temperature for one hour
  2. customthe reaction
  3. extractionextracted with dichloromethane
  4. customthe organic phase decanted off
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe residue obtained
  8. customwas purified by chromatography on a silica column
  9. washeluted with a mixture of heptane and ethyl acetate (80/20)
  10. custom145 mg (73%) of the expected aldehyde of melting point 98-9° C. were recovered

Sources & evidence

ORD record
ord-319304bd9ac74cc093756c25d9f85d32
Source dataset
uspto-grants-2000_12
Patent number
US06162815

Reaction notes

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