Tetraethoxysilane → HCID 22050002, compound

HRID 1831969Notes

Reaction equation

HRID 1831969 reaction equation
[Br:1][C:2]1[C:3](=[O:19])[NH:4][C:5](C)=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13](F)=[CH:12][C:11]=1F.[F-].[Cs+].C(O[Si](OCC)(OCC)OCC)C.[C:35]([O:39][CH2:40][CH3:41])(=[O:38])[CH:36]=[CH2:37]>O1CCCC1>[CH2:9]([O:8][C:7]1[CH:6]=[CH:5][N:4]([CH2:37][CH2:36][C:35]([O:39][CH2:40][CH3:41])=[O:38])[C:3](=[O:19])[C:2]=1[Br:1])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 6517TetraethoxysilaneHCID 8821Ethyl AcrylateHCID 25953Cesium fluorideHCID 220504293-bromo-4-[(2,4-difluorobenzyl)oxy]-6-methylpyridin-2(1H)-one

Product 1

HCID 22050002HCID 22050002, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-bromo-4-[(2,4-difluorobenzyl)oxy]-6-methylpyridin-2(1H)-one (0.50 g, 1.78 mmol) and cesium fluoride (0.0027 g, 0.178 mmol) were suspended in tetrahydrofuran (10 mL) followed by dropwise addition of tetraethylortho silicate (0.37 g, 1.78 mmol) at room temperature. After stirring for 10 minutes at room temperature, ethyl acrylate (0.23 g, 2.32 mmol) was added dropwise and the reaction stirred at room temperature overnight. The reaction mixture was filtered through a pad of Celite®. The filtrate was concentrated and the resulting residue subjected to chromatography (silica gel, ethyl acetate with 10% methanol/hexanes) to afford a white solid (0.62 g, 92%). 1H NMR (400 MHz, CDCl3) δ 7.42 (d, J=7.79 Hz, 1H), 7.41-7.29 (m, 5H), 6.03 (d, J=7.65 Hz, 1H), 5.20 (s, 2H), 4.17 (t, J=5.98 Hz, 2H), 4.07 (q, J=7.16 Hz, 2H), 2.83 (t, J=5.98 Hz, 2H), 1.19 (t, J=7.18 Hz, 3H). ES-HRMS m/z 380.0523 (M+H C17H18BrNO4 requires 380.0492).

Workup

  1. stirringthe reaction stirred at room temperature overnight
  2. filtrationThe reaction mixture was filtered through a pad of Celite®
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-6aa1c7d5c55542db98abe06df2247b67
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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