Potassium Carbonate → HCID 53328682, compound

HRID 2042935Notes

Reaction equation

HRID 2042935 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][C:9]2[S:10][C:11]([C:14]3[O:15][CH:16]=[CH:17][CH:18]=3)=[CH:12][N:13]=2)=[CH:6][C:5]([C@H:19]2[C@H:24]([OH:25])[C@@H:23]([OH:26])[C@H:22]([OH:27])[C@@H:21]([CH2:28][OH:29])[O:20]2)=[C:4]([OH:30])[CH:3]=1.Br[CH2:32][CH2:33][O:34][CH3:35].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[C:7]([CH2:8][C:9]2[S:10][C:11]([C:14]3[O:15][CH:16]=[CH:17][CH:18]=3)=[CH:12][N:13]=2)=[CH:6][C:5]([C@H:19]2[C@H:24]([OH:25])[C@@H:23]([OH:26])[C@H:22]([OH:27])[C@@H:21]([CH2:28][OH:29])[O:20]2)=[C:4]([O:30][CH2:32][CH2:33][O:34][CH3:35])[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 53327913HCID 53327913, compound

Product 1

HCID 53328682HCID 53328682, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of phenol 63 (205 mg, 0.451 mmol) in acetone (10 mL) was added bromoethylmethyl ether (1.6 mL, 15.8 mmol) and K2CO3 (2.3 g, 15.8 mmol) at room temperature. The mixture was stirred at 50° C. for 15 h. The mixture was cooled to room temperature and filtered off through the celite. The filtrate was concentrated in vacuo. The residue was purified by prep HPLC (C18) to provide the titled compound 64 (42 mg, 19%).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered off through the celite
  3. concentrationThe filtrate was concentrated in vacuo
  4. customThe residue was purified by prep HPLC (C18)

Sources & evidence

ORD record
ord-df8a428edb9c4d2898f42a3635ff5de5
Source dataset
uspto-grants-2013_11
Patent number
US08586550B2

Reaction notes

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