Dimethyl Sulfoxide → HCID 14537110, compound

HRID 2165188Notes

Reaction equation

HRID 2165188 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][O:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([O:23][CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][O:25]2)=[C:15]([CH2:30][CH2:31][CH2:32][OH:33])[CH:14]=1.C(N(CC)CC)C>C(Cl)Cl>[CH:32]([CH2:31][CH2:30][C:15]1[CH:14]=[C:13]([O:12][CH3:11])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]=1[O:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][O:25]1)=[O:33]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 14537109HCID 14537109, compound

Product 1

HCID 14537110HCID 14537110, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

An oven-dried 25 ml 2-necked (14/20) round bottom flask, equipped with magnetic stirring bar nitrogen inlet and serum cap, is charged with a solution of oxalyl chloride (61 μl) in 2 ml methylene chloride. This solution is placed under a nitrogen atmosphere and cooled to -60° C. to -50° C. Dimethylsulfoxide (99 μl) is added (neat) dropwise to give a colorless solution. After 2.3 min a solution of 3-[4-methoxy-1-[(tetrahydro-2H-pyran-2-yl)oxy]-2-naphthalenyl]-1-propanol (0.19 g) in 1 ml methylene chloride is added dropwise. The resulting mixture is stirred at -60° C. to -50° C. for 15 min and then treated with triethylamine (0.44 ml). This gives rise to a yellow colored milky suspension. The cooling bath is removed and the stirred mixture is allowed to warm to room temperature at which time the mixture is diluted with water and extracted with ether. The organic phase is washed three times with water (after adjusting the pH to 7 with 10% aqueous sodium bisulfate), dried with magnesium sulfate, filtered and concentrated to give 0.18 g of the crude title compound as an orange colored oil.

Workup

  1. customserum cap
  2. temperaturecooled to -60° C. to -50° C
  3. customto give a colorless solution
  4. customThe cooling bath is removed
  5. additionis diluted with water
  6. extractionextracted with ether
  7. washThe organic phase is washed three times with water (
  8. dry with materialdried with magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-6e60cef592bf4aea8743620866d6b766
Source dataset
uspto-grants-1990_07
Patent number
US04939169

Reaction notes

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