Potassium Carbonate → HCID 69764339, compound

HRID 1373769Notes

Reaction equation

HRID 1373769 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:6]=1[N:12]1[C:20](=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]1=[O:22])[CH:2]=[CH2:3].Br[CH2:24][CH2:25][O:26][CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][O:28]1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:24][CH2:25][O:26][CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][O:28]2)=[CH:7][C:6]=1[N:12]1[C:13](=[O:22])[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:20]1=[O:21])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 69633424HCID 69633424, compound

Product 1

HCID 69764339HCID 69764339, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of Example 84A (0.69 g, 2.34 mmol), 2-(2-bromoethoxy)tetrahydro-2H-pyran (1.41 mL, 9.34 mmol) and K2CO3 (1.61 g, 11.68 mmol) in acetone (20 mL) was refluxed overnight and cooled. The solution was filtered, dried with silica gel powder (10 g). 20% Ethyl acetate in hexanes (1 L) and 30% ethyl acetate in hexanes (1 L) were used to run flash chromatography. The title compound was obtained (265.3 mg, 27%). MS (APCI) m/z 424 (M+H)+.

Workup

  1. temperaturecooled
  2. filtrationThe solution was filtered
  3. customdried with silica gel powder (10 g)

Sources & evidence

ORD record
ord-b501757e9d904fb3859f39a06cd97b31
Source dataset
uspto-grants-2007_01
Patent number
US07163939B2

Reaction notes

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