Pyridine → HCID 19359917, compound

HRID 376826Notes

Reaction equation

HRID 376826 reaction equation
[CH:1]1([Sn:7]([CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH:14](O)[CH3:15])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N1C=CC=CC=1.CS(Cl)(=O)=O.[N-:40]=[N+:41]=[N-:42].[Na+]>O.CN(C)C=O>[CH:1]1([Sn:7]([CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH:14]([N:40]=[N+:41]=[N-:42])[CH3:15])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 19359512Tricyclohexyl [o-(1-hydroxyethyl)phenyl]tin

Product 1

HCID 19359917HCID 19359917, compoundYield 27.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

997 mg of tricyclohexyl [o-(1-hydroxyethyl)phenyl]tin (2.04 mmol) and 20 ml of pyridine were mixed together in a 20 ml two-neck flask, then 269 mg of methane sulfonyl chloride (2.35 mmol) was added dropwise thereto. After the mixture was stirred for 22 hours at a room temperature, a brown-colored solid, which had been obtained by concentrating the reaction solution under reduced pressure, was dissolved in 10 ml of dimethylformamide. Subsequently, 10 ml of a dimethylformamide solution containing 354 mg of sodium azide (5.44 mmol) was added dropwise, and the mixture was then refluxed for 3 hours. After the mixture was cooled to 0° C., and 20 ml of water was added, the organic substance was extracted with 30 ml of ether three times. After the ether layer was washed with 30 ml of a saturated brine, and dried over sodium sulfate, the solvent was removed under reduced pressure to yield a crude product. The resultant crude product was purified by column chromatography on silica gel (for which, 50 g of silica gel, and hexane, as a devleoping solvent were employed) to yield 288 mg of the final product (0.559 mmol).

Workup

  1. customa brown-colored solid, which had been obtained
  2. concentrationby concentrating the reaction solution under reduced pressure
  3. dissolutionwas dissolved in 10 ml of dimethylformamide
  4. additionwas added dropwise
  5. temperaturethe mixture was then refluxed for 3 hours
  6. temperatureAfter the mixture was cooled to 0° C.
  7. extractionthe organic substance was extracted with 30 ml of ether three times
  8. washAfter the ether layer was washed with 30 ml of a saturated brine
  9. dry with materialdried over sodium sulfate
  10. customthe solvent was removed under reduced pressure
  11. customto yield a crude product
  12. customThe resultant crude product was purified by column chromatography on silica gel (for which, 50 g of silica gel, and hexane

Sources & evidence

ORD record
ord-994da6fc8bf44c77bf6a1b1b67264232
Source dataset
uspto-grants-2000_02
Patent number
US06022822

Reaction notes

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