2,6-Lutidine → HCID 59331540, compound

HRID 1881947Notes

Reaction equation

HRID 1881947 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]([OH:18])[CH2:9][O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])=[CH:4][CH:3]=1.N1C(C)=CC=CC=1C.FC(F)(F)S(O[Si:33]([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34])(=O)=O.C(=O)([O-])O.[Na+]>ClCCl>[Si:33]([O:18][CH:8]([C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[N:7][CH:6]=1)[CH2:9][O:10][Si:11]([C:14]([CH3:15])([CH3:17])[CH3:16])([CH3:13])[CH3:12])([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34]

Participants

6

Reactant 4

HCID 79372,6-LutidineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 516892Sodium BicarbonateHCID 59331552HCID 59331552, compound

Product 1

HCID 59331540HCID 59331540, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(6-bromopyridin-3-yl)-2-{[tert-butyl(dimethyl)silyl]oxy}ethanol (1.58 g) and 2,6-lutidine (0.83 mL) in dichloromethane (15 mL) was cooled to 0° C., tert-butyl(dimethyl)silyl trifluoromethanesulfonate (1.31 mL) was added dropwise, and the mixture was stirred for 1 hr. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with diethyl ether. The extract was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (1.79 g, yield 84%) was obtained as a pale-yellow amorphous solid from a fraction eluted with ethyl acetate-hexane (1:19, volume ratio).

Workup

  1. extractionthe mixture was extracted with diethyl ether
  2. washThe extract was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-62bce150f2c84affa7b7d62435adb63d
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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