Cesium carbonate → HCID 86653232, compound

HRID 2360358Notes

Reaction equation

HRID 2360358 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:16]([O:23][C:24]1[CH:25]=[C:26]([OH:30])[CH:27]=[CH:28][CH:29]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C)C=O>[CH2:16]([O:23][C:24]1[CH:25]=[C:26]([CH:27]=[CH:28][CH:29]=1)[O:30][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 680234-FluorobenzaldehydeHCID 138048Benzyl 3-hydroxyphenyl ether

Product 1

HCID 86653232HCID 86653232, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a stirring solution of p-fluorobenzaldehyde (6.15 mmol, 0.763 g) in dimethylformamide (20.5 mL) was added cesium carbonate (4.1 mmol, 1.33 g) and 38 (4.1 mmol, 0.819 g). This solution was heated to 90° C. and monitored with TLC. When complete, the reaction mixture was cooled to room temperature and filtered through a fritted funnel. The filtrate was then diluted with ethyl acetate (200 mL) and extracted with eight 15 mL portions of water and one 10 mL portion of brine. The organic layer was dried over magnesium sulfate, evaporated to dryness and purified with flash chromatography to yield 0.930 g (3.05 mmol) of the title product. 1H NMR (500 MHz, CDCl3) δ 9.93 (s, 1H), 7.85 (d, J=8.6, 2H), 7.55-7.22 (m, 6H), 7.07 (d, J=8.7, 2H), 6.86 (d, J=8.3, 1H), 6.71 (dd, J=5.2, 10.7, 2H), 5.06 (s, 2H). 13C NMR (126 MHz, CDCl3) δ 190.79, 162.93, 160.50, 156.39, 131.94, 130.61, 128.66, 128.15, 127.52, 117.78, 112.66, 111.44, 107.25, 70.18.

Workup

  1. temperatureWhen complete, the reaction mixture was cooled to room temperature
  2. filtrationfiltered through a fritted funnel
  3. additionThe filtrate was then diluted with ethyl acetate (200 mL)
  4. extractionextracted with eight 15 mL portions of water and one 10 mL portion of brine
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. customevaporated to dryness
  7. custompurified with flash chromatography

Sources & evidence

ORD record
ord-7a9ab9a843cb4e8187144d559e42aa31
Source dataset
uspto-grants-2014_04
Patent number
US08686046B2

Reaction notes

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