Pyridine → HCID 90071917, compound

HRID 927928Notes

Reaction equation

HRID 927928 reaction equation
[O:1]([Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])S(C(F)(F)F)(=O)=O.[Br:16][C:17]1[CH:21]=[CH:20][O:19][C:18]=1[CH2:22]O.N1C=CC=CC=1>C(Cl)Cl>[Br:16][C:17]1[CH:21]=[CH:20][O:19][C:18]=1[CH2:22][O:1][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 1049PyridineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 19437133(3-Bromofuran-2-yl)methanol2×

Product 1

HCID 90071917HCID 90071917, compoundYield 102.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

tert-Butyldimethylsilanyl triflate (17.13 g) was added slowly to a stirred, cooled solution of 3-bromo-2-hydroxymethylfuran (Intermediate 39, 10.1 g) in DCM (160 mL) and pyridine (9.57 g) while maintaining the temperature at 0° C. The mixture was allowed to warm to room temperature and stirred for 1 hour. The mixture was washed with aqueous citric acid solution, brine, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness to give 3-bromo-2-(tert-butyldimethylsilanyloxymethyl)furan (17.1 g).

Workup

  1. temperatureto warm to room temperature
  2. washThe mixture was washed with aqueous citric acid solution, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-4ed936c690ff45d8b92d0f2cc1e95bde
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

Loading…