Water → HCID 11012298, compound

HRID 1276820Notes

Reaction equation

HRID 1276820 reaction equation
[Br:1][CH2:2][C:3]([CH2:7][CH:8]1[CH:12]=[CH:11][CH:10]=[CH:9]1)([CH3:6])[CH2:4][OH:5].C(N(CC)CC)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22].O>C(Cl)Cl>[CH3:20][S:21]([O:5][CH2:4][C:3]([CH2:2][Br:1])([CH2:7][CH:8]1[CH:12]=[CH:11][CH:10]=[CH:9]1)[CH3:6])(=[O:23])=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride2×HCID 11770285HCID 11770285, compound

Product 1

HCID 11012298HCID 11012298, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In a 200 ml Schlenk tube fitted with a septum, 6.97 g of crude product 3 and 4.35 ml (45 mmol) of triethylamine were dissolved in 100 ml of methylene chloride. At 0° C., 2.37 ml (31 mmol) of methanesulfonyl chloride were injected over a period of 2 minutes. After half the methanesulfonyl chloride had been added, a colorless precipitate formed. The suspension was held at this temperature for another half hour and was then stirred for 2 hours at room temperature. The reaction solution was subsequently hydrolyzed with 20 ml of water. The phases were separated and the aqueous phase was extracted three times with 20 ml of methylene chloride. The combined organic phases were washed with sodium chloride solution until neutral and dried over sodium sulfate. Removal of the solvent in an oil pump vacuum gave a slightly brownish oil which was dissolved in methylene chloride and absorbed on kieselguhr. This was followed by flash chromatography on a silical gel column (4*25 cm; PE/THF in a ratio of 8:2; RF =0.42). Evaporation of the product fractions in an oil pump vacuum gave 5.9 g (66%) of 4 as a colorless oil.

Workup

  1. customa colorless precipitate formed
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted three times with 20 ml of methylene chloride
  4. washThe combined organic phases were washed with sodium chloride solution until neutral and
  5. dry with materialdried over sodium sulfate
  6. customRemoval of the solvent in an oil pump vacuum
  7. customgave a slightly brownish oil which
  8. customabsorbed on kieselguhr
  9. customEvaporation of the product fractions in an oil pump vacuum

Sources & evidence

ORD record
ord-e02d3c66b540437096624a13ef70e523
Source dataset
uspto-grants-2000_12
Patent number
US06166234

Reaction notes

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