2,6-Lutidine → HCID 131716836, compound

HRID 1085925Notes

Reaction equation

HRID 1085925 reaction equation
[S:1]([C:5]1[CH:11]=[CH:10][C:8]([CH3:9])=[CH:7][CH:6]=1)([O-:4])(=[O:3])=[O:2].N1C(C)=CC=CC=1C.[O:20]([Si:28](C(C)(C)C)(C)C)S(C(F)(F)F)(=O)=O>C(Cl)Cl.O>[S:1]([C:5]1[CH:11]=[CH:10][C:8]([CH3:9])=[CH:7][CH:6]=1)([O:4][O:20][SiH3:28])(=[O:3])=[O:2]

Participants

6

Reactant 3

HCID 79372,6-LutidineHCID 85570p-ToluenesulfonateHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonate

Product 1

HCID 131716836HCID 131716836, compound

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 140 mg of the primary tosylate 26, 0.10 ml of 2,6-lutidine and 0.10 ml of t-butyldimethylsilyl triflate in 8 ml of methylene chloride was stirred at 0° C. for 1 hour. A few drops of water were added and the mixture concentrated under vacuum. The residue was diluted with diethyl ether and the solution filtered thru silica gel. The filtrate was concentrated under vacuum and chromatography of the residue over silica gel (6 hexanes: 1 EtOAc) provided the title compound.

Workup

  1. concentrationthe mixture concentrated under vacuum
  2. additionThe residue was diluted with diethyl ether
  3. filtrationthe solution filtered
  4. concentrationThe filtrate was concentrated under vacuum and chromatography of the residue over silica gel (6 hexanes: 1 EtOAc)

Sources & evidence

ORD record
ord-7b7acd80bc964df192b898e5d5abcc0c
Source dataset
uspto-grants-1991_04
Patent number
US05011943

Reaction notes

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