Triethylamine → 2-(Tert-butyldimethylsilyloxy)furan

HRID 480035

Reaction equation

HRID 480035 reaction equation
[O:1]1[CH2:5][CH:4]=[CH:3][C:2]1=[O:6].C(N(CC)CC)C.[Si:14](OS(C(F)(F)F)(=O)=O)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]>ClCCl>[Si:14]([O:6][C:2]1[O:1][CH:5]=[CH:4][CH:3]=1)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 103412(5H)-FuranoneHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonate

Product 1

HCID 108673032-(Tert-butyldimethylsilyloxy)furan

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a freshly distilled solution of 2(5H)-furanone (2.86 g, 34 mmol) in dichloromethane (20 ml), distilled triethylamine (6.6 ml. 47.4 mmol) is added under argon at 0° C. and then rapidly followed by tert-butyldimehylsilyltrifluoromethane sulfonate (8.6 ml, 37.3 mmol) The reaction mixture is allowed to return to room temperature and the stirring is maintained for two hours. The solvent is then removed under reduced pressure and the oily residue is purified by flash chromatography on silica gel (ethyl acetate-heptane, 1:9) in order to thus obtain compound 10 (Z=O) in the form of a slightly colored oil (5.3 g, 79%). The spectroscopic data for this compound (1H and 13C NMR) are identical to those described in the literature (G. Rassu, Z. Zanardi, L. Battistini, E. Gaetani, G. Casiraghi, J. Med. Chem ., 1997, 40, 168).

Workup

  1. additionis added under argon at 0° C.
  2. customto return to room temperature
  3. temperaturethe stirring is maintained for two hours
  4. customThe solvent is then removed under reduced pressure
  5. customthe oily residue is purified by flash chromatography on silica gel (ethyl acetate-heptane, 1:9) in order to thus obtain compound 10 (Z=O) in the form of a slightly colored oil (5.3 g, 79%)

Sources & evidence

ORD record
ord-f42274949c0f4f5a89dca6573bc1fbee
Source dataset
uspto-grants-2003_11
Patent number
US06649626B1

Linked notes

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