Potassium Carbonate → HCID 67428436, compound

HRID 1667774Notes

Reaction equation

HRID 1667774 reaction equation
[F:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[CH:4][C:5]([O:9][CH3:10])=[C:6]([OH:8])[CH:7]=1.Br[CH2:15][CH2:16][O:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][O:19]1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CN(C)C=O>[F:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[CH:4][C:5]([O:9][CH3:10])=[C:6]([CH:7]=1)[O:8][CH2:15][CH2:16][O:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][O:19]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 67426546HCID 67426546, compound

Product 1

HCID 67428436HCID 67428436, compoundYield 58.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.374 g (2 mmole) of 5-fluoro-2-methoxy-4-nitro-phenol, 0.439 g (2.10 mmole) of 2-(2-bromo-ethoxy)-tetrahydro-pyran, 0.828 g (6.0 mmole) of potassium carbonate and 5 mL of dimethylformamide was heated at 80 degrees for 4 hours. The cooled mixture was poured into 50 mL of dilute ammonium chloride solution and extracted three times with 25 mL of ethyl acetate. The combined organic extracts were washed three times with 25 mL of water, once with 25 mL of brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with ethyl acetate-hexanes (gradient 20:80-30:70) to give 0.370 g of 2-[2-(5-fluoro-2-methoxy-4-nitro-phenoxy)-ethoxy]-tetrahydro-pyran (IV.44) as a yellow oil.

Workup

  1. temperaturewas heated at 80 degrees for 4 hours
  2. extractionextracted three times with 25 mL of ethyl acetate
  3. washThe combined organic extracts were washed three times with 25 mL of water
  4. dry with materialonce with 25 mL of brine, dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with ethyl acetate-hexanes (gradient 20:80-30:70)

Sources & evidence

ORD record
ord-a12e779b4ae7417f9a4f0adfb6261062
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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