Triethylamine → HCID 66759725, compound

HRID 2063813Notes

Reaction equation

HRID 2063813 reaction equation
C(N(CC)CC)C.FC(F)(F)S([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])(=O)=O.[Br:23][C:24]1[C:25]([CH3:36])=[C:26]([CH3:35])[C:27]2[O:31][CH2:30][C:29](=O)[C:28]=2[C:33]=1[CH3:34].O.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.C1(C)C=CC=CC=1>[Br:23][C:24]1[C:25]([CH3:36])=[C:26]([CH3:35])[C:27]2[O:31][CH:30]=[C:29]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[C:28]=2[C:33]=1[CH3:34]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 23114238HCID 23114238, compoundHCID 86585896Sodium bicarbonate water

Product 1

HCID 66759725HCID 66759725, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (2.15 g, 21.2 mmol) and tert-butyldimethylsilyl trifluoromethanesulfonate (4.68 g, 17.7 mmol) were sequentially added to a solution of toluene (100 mL) containing 5-bromo-4,6,7-trimethyl-1-benzofuran-3(2H)-one (3.00 g, 11.8 mmol) synthesized in Reference Example 45, and the mixture was stirred at room temperature for 1 hour. The resulting mixture was poured into saturated sodium bicarbonate water, and extraction was performed using ethyl acetate. The extract was washed with saturated saline, and dried using anhydrous magnesium sulfate, followed by concentration under reduced pressure. The residue was purified by silica gel chromatography (hexane-ethyl acetate 99:1 to 94/6) to give 4.14 g of the title compound (yield: 95%).

Workup

  1. customsynthesized in Reference Example 45
  2. washThe extract was washed with saturated saline
  3. customdried
  4. concentrationfollowed by concentration under reduced pressure
  5. customThe residue was purified by silica gel chromatography (hexane-ethyl acetate 99:1 to 94/6)

Sources & evidence

ORD record
ord-062a0fc10173478fbb2e98498165b4bb
Source dataset
uspto-grants-2012_10
Patent number
US08288390B2

Reaction notes

Loading…