Potassium Carbonate → HCID 67314274, compound

HRID 1012605Notes

Reaction equation

HRID 1012605 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH3:9].Br[CH2:11][CH2:12][O:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][O:15]1.C([O-])([O-])=O.[K+].[K+].[OH-].[Na+]>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:11][CH2:12][O:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)=[CH:4][C:3]=1[CH3:9]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 728574-Bromo-m-cresolHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyran

Product 1

HCID 67314274HCID 67314274, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 4-bromo-3-methyl-phenol (10.6 g, 56.9 mmol) and 2-(2-bromo-ethoxy)-tetrahydro-pyran (11.9, 56.9 mmol) were dissolved in dry DMF (25 mL). K2CO3 (19.7 g, 142 mmol) was added and the resulting reaction mixture was stirred at 80° C. for 48 h. The reaction mixture was cooled to RT and poured into a mixture of EtOAc and aqueous NaOH (2 N). The organic phase was separated, dried (MgSO4), filtered, and concentrated in vacuo to give the crude product. The crude product was purified by flash chromatography using EtOAc/pentane 1:20 as the eluent to afford the title compound as colourless oil.

Workup

  1. customthe resulting reaction mixture
  2. temperatureThe reaction mixture was cooled to RT
  3. customThe organic phase was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give the crude product
  8. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-042b04ec46c44ba5b13639b980ff68a8
Source dataset
uspto-grants-2011_07
Patent number
US07977387B2

Reaction notes

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