Potassium Carbonate → HCID 21048991, compound

HRID 2212380Notes

Reaction equation

HRID 2212380 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2([C:27]3[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:28]=3[F:34])[CH2:16][CH2:15][CH:14]([CH2:17][C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[OH:26])=[O:19])[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.Br[CH2:36][C:37]([O:39][CH3:40])=[O:38].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:40][O:39][C:37](=[O:38])[CH2:36][O:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[C:18](=[O:19])[CH2:17][CH:14]1[CH2:13][CH2:12][C:11]([S:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)(=[O:10])=[O:9])([C:27]2[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:28]=2[F:34])[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 21963954HCID 21963954, compound

Product 1

HCID 21048991HCID 21048991, compoundYield 86.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of this phenol (100 mg, 0.20 mmol) in acetone (10 mL) under nitrogen was added methyl bromoacetate (21 μL, 0.22 mmol) and potassium carbonate (55 mg, 0.40 mmol). The mixture was heated to reflux for 14 h., cooled to room temperature, filtered and the filtrate evaporated to afford a residue (100 mg) which was purified using preparative thin layer chromatography eluting with diethyl ether:dichloromethane:iso-hexane 1:1:5 to give the desired product (25 mg).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 14 h.
  3. filtrationfiltered
  4. customthe filtrate evaporated

Sources & evidence

ORD record
ord-e91a59c6bc4a427595d999e5ac8107de
Source dataset
uspto-grants-2006_09
Patent number
US07101895B2

Reaction notes

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