Ethyl Bromide → HCID 58934952, compound

HRID 855019Notes

Reaction equation

HRID 855019 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[OH:13])[O:9][CH:8]([C:14]([F:17])([F:16])[F:15])[C:7]([C:18]([OH:20])=[O:19])=[CH:6]2)[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:27](Br)[CH3:28].C(OCC)(=O)C>CN(C)C=O>[CH2:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[OH:13])[O:9][CH:8]([C:14]([F:15])([F:16])[F:17])[C:7]([C:18]([O:20][CH2:27][CH3:28])=[O:19])=[CH:6]2)[CH3:2]

Participants

6

Reactant 4

HCID 6332Ethyl BromideHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 58934586HCID 58934586, compound

Product 1

HCID 58934952HCID 58934952, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.3 g (1.04 mmol) of 6-ethyl-7-hydroxy-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid in 5 mL of anhydrous dimethylformamide was added 255 mg (0.78 mmol) of cesium carbonate in one portion, followed by addition of 103 uL (1.7 mmol) of ethyl bromide. The reaction was stirred at room temperature overnight. The reaction was added to 100 mL of ethyl acetate. The organic phase was washed with brine three times, and dried over anhydrous magnesium sulfate. After removing the volatiles, the residue was purified by silica chromatography with EtOAc/hexane (3:7) to afford 0.21 g (67%) of a light yellow solid: 1H NMR (CDCl3/400 MHz) 7.68(s, 1H), 7.00(s, 1H), 6.42(s, 1H), 5.63 (q, J=7.2 Hz, 1H), 5.38(s, 1H), 4.28(m, 2H), 2.54(q, J=7.2 Hz, 2H), 1.31(t, J=7.2 Hz, 3H), 1.20(t, J=7.6 Hz, 3H), MS (ESI+) 317 (M+1, 100).

Workup

  1. washThe organic phase was washed with brine three times
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customAfter removing the volatiles
  4. customthe residue was purified by silica chromatography with EtOAc/hexane (3:7)

Sources & evidence

ORD record
ord-53b39b10beba45e3bd561906a0251445
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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