Dimethyl Sulfoxide → HCID 10380396, compound

HRID 1494131Notes

Reaction equation

HRID 1494131 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[N:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][CH2:18][CH2:19][CH:20]([OH:32])[CH2:21][CH2:22][CH2:23][CH2:24][O:25][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][O:27]2)[CH:12]=1>C(Cl)Cl>[N:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][CH2:18][CH2:19][C:20](=[O:32])[CH2:21][CH2:22][CH2:23][CH2:24][O:25][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][O:27]2)[CH:12]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 10335383HCID 10335383, compound

Product 1

HCID 10380396HCID 10380396, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of 1.62 mL (22.73 mmol) of dimethylsulfoxide in 60 mL dry methylene chloride is cooled to -78° C. and 1.44 mL (16.53 mmol) oxalyl chloride is added dropwise. The mixture is stirred 0.5 hour at -78° C. and a solution of 1.0 g (3.31 mmol) of 1-(3-pyridyl)-4-hydroxy-8-(2-tetrahydropyranyloxy)octane in 15 mL dry methylene chloride is added and the mixture is stirred for 10 minutes at -78° C. The mixture is warmed to -60° C. and maintained for 15 minutes at that temperature. The reaction is quenched by the addition of 6.9 mL triethylamine. The cold bath is removed and the reaction allowed to warm to room temperature. The reaction mixture is extracted with 150 mL methylene chloride and washed with saturated sodium bicarbonate solution. The organic phase is dried, filtered, concentrated and chromatographed using 3:2 ethyl acetate, hexane to yield 1-(3-pyridyl)-4-oxo-8-(2-tetrahydropyranyloxy)octane; NMR (CDCl3): delta 2.6 (t,2H), 2.4 (t,4H).

Workup

  1. stirringthe mixture is stirred for 10 minutes at -78° C
  2. temperatureThe mixture is warmed to -60° C.
  3. temperaturemaintained for 15 minutes at that temperature
  4. customThe reaction is quenched by the addition of 6.9 mL triethylamine
  5. customThe cold bath is removed
  6. temperatureto warm to room temperature
  7. extractionThe reaction mixture is extracted with 150 mL methylene chloride
  8. washwashed with saturated sodium bicarbonate solution
  9. customThe organic phase is dried
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customchromatographed

Sources & evidence

ORD record
ord-0f4b4ab6881c4b0a9d7e56a9f964ce5c
Source dataset
uspto-grants-1991_06
Patent number
US05025025

Reaction notes

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