Dimethyl Sulfoxide → HCID 21078411, compound

HRID 1374915Notes

Reaction equation

HRID 1374915 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=1.[O:15]=O.[K+].O1CCOCCOCCOCCOCCOCC1.C(OCC)C.[CH3:41][S:42](C)=O>>[OH:15][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:7]=1[S:42][CH3:41]

Participants

6

Reactant 5

HCID 679Dimethyl SulfoxideHCID 3283Diethyl EtherHCID 2855718-Crown-6HCID 6154112030-88-5HCID 232635923-Bromo-5-phenoxypyridine

Product 1

HCID 21078411HCID 21078411, compound

Procedure

3-Bromo-5-phenoxypyridine (0.50 g) and potassium superoxide (1.42 g) in dry dimethyl sulphoxide (100 ml) containing 1,4,7,10,13,16-hexaoxacyclooctadecane (3.20 g) were stirred at ambient temperature under an atmosphere of nitrogen for 18 hours. The solvent was evaporated under reduced pressure to a small volume and the mixture diluted with water, washed with ethyl acetate (twice) and the basic aqueous phase was acidified to pH 4 with dilute aqueous hydrochloric acid. The mixture was extracted with ethyl acetate (three times), the extracts were combined and washed with water (four times), dried over magnesium sulphate and evaporated under reduced pressure to give an oil. The oil was fractionated by chromatography (silica; diethyl ether) to give the required product, 0.19 g, as a colourless solid, m.p. 131–133° C.

Workup

  1. customThe solvent was evaporated under reduced pressure to a small volume
  2. additionthe mixture diluted with water
  3. washwashed with ethyl acetate (twice) and the basic aqueous phase
  4. extractionThe mixture was extracted with ethyl acetate (three times)
  5. washwashed with water (four times)
  6. dry with materialdried over magnesium sulphate
  7. customevaporated under reduced pressure
  8. customto give an oil

Sources & evidence

ORD record
ord-9d62d46635e6437589a1b87d7f8f552c
Source dataset
uspto-grants-2007_01
Patent number
US07166621B2

Reaction notes

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