2,6-Lutidine → HCID 18753697, compound

HRID 1838446Notes

Reaction equation

HRID 1838446 reaction equation
[C:1]([O:4][O:5][CH:6]1[CH2:10][CH:9]([OH:11])[CH:8]=[CH:7]1)(=[O:3])[CH3:2].N1C(C)=CC=CC=1C.FC(F)(F)S(O[Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])(=O)=O>C(Cl)Cl>[C:1]([O:4][O:5][CH:6]1[CH2:10][CH:9]([O:11][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])[CH:8]=[CH:7]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 18753705HCID 18753705, compound

Product 1

HCID 18753697HCID 18753697, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 4-hydroxy-cyclopent-2-enyloxy acetate (4.1 g, 29 mmol) in CH2Cl2 (35 mL) and 2,6-lutidine (8.2 mL, 67 mmol) was added t-butyldimethylsilyl trifluoromethanesulfonate (10 mL, 44 mmol) at 0-5° C. The reaction mixture was stirred at r.t. for 1 hour. It was diluted with CH2Cl2, washed (brine), dried (Na2SO4), filtered and concentrated Column chromatography (silica gel, 5:1 hexanes:diethylether) gave desired product (5.1 g, 69%). 1H NMR (CDCl3, 400 MHz) δ; 5.88 (m, 1H); 5.84 (m, 1H); 5.42 (t, 1H); 4.64 (t, 1H); 2.80 (m, 1H); 2.02 (s, 3H); 1.59 (m, 1H); 0.83 (s, 9H); 0.04 (s, 6H).

Workup

  1. washwashed (brine)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated Column chromatography (silica gel, 5:1 hexanes:diethylether)

Sources & evidence

ORD record
ord-3a72668237ea42cb893002968f20869a
Source dataset
uspto-grants-2004_01
Patent number
US06673809B2

Reaction notes

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