Cesium carbonate → Ethyl 4-[(4-{[3-methyl-6-(methyloxy)-2-phenyl-1-naphthalenyl]oxy}phenyl)oxy]butanoate

HRID 1993012Notes

Reaction equation

HRID 1993012 reaction equation
[CH3:1][C:2]1[C:3]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:4]([O:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[CH:7][CH:6]=2.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:35][CH2:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39]>CN(C=O)C>[CH3:1][C:2]1[C:3]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:4]([O:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:35][CH2:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])=[CH:17][CH:16]=2)[C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[CH:7][CH:6]=2

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 76300Ethyl 4-bromobutyrateHCID 685394164-{[3-Methyl-6-(methyloxy)-2-phenyl-1-naphthalenyl]oxy}phenol

Product 1

HCID 68536177Ethyl 4-[(4-{[3-methyl-6-(methyloxy)-2-phenyl-1-naphthalenyl]oxy}phenyl)oxy]butanoateYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A round-bottomed flask was charged with 4-{[3-methyl-6-(methyloxy)-2-phenyl-1-naphthalenyl]oxy}phenol (233) (0.300 g, 0.842 mmol), Cs2CO3 (0.824 g, 2.53 mmol), DMF (4 mL), and ethyl 4-bromobutanoate (0.602 mL, 4.21 mmol) under N2. The reaction mixture was refluxed for 15 h and cooled at room temperature. Reaction mixture was partitioned between water and EtOAC (1:1, 100 mL) and the layers were separated. The aqueous phase was further extracted with EtOAc (2×30 mL). The combined organic layer was washed with brine (1×25 mL), dried (Na2SO4), and then concentrated under reduced pressure to afford the crude product. The product was purified by SiO2 column chromatography using hexanes:EtOAc (19:1 to 9:1) as an eluent to give 0.356 g (90%) of the title compound (288) as a colorless oil. LCMS (ESI) m/z 493.27 (M+Na)+.

Workup

  1. temperatureThe reaction mixture was refluxed for 15 h
  2. customReaction mixture
  3. customwas partitioned between water and EtOAC (1:1, 100 mL)
  4. customthe layers were separated
  5. extractionThe aqueous phase was further extracted with EtOAc (2×30 mL)
  6. washThe combined organic layer was washed with brine (1×25 mL)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated under reduced pressure
  9. customto afford the crude product
  10. customThe product was purified by SiO2 column chromatography

Sources & evidence

ORD record
ord-406eeda2813d453590a870655ce75aa6
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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