Cesium carbonate → HCID 86690867, compound

HRID 1465565Notes

Reaction equation

HRID 1465565 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][CH2:11][O:12][CH3:13])=[CH:4][CH:3]=1.[OH:14][C:15]1[CH:20]=[C:19]([CH3:21])[C:18]([C:22](=[O:24])[CH3:23])=[C:17]([CH3:25])[CH:16]=1.Cl.CN(C)CC(O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.[Cu](I)I.O>[CH3:13][O:12][CH2:11][CH2:10][CH2:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([O:14][C:15]2[CH:16]=[C:17]([CH3:25])[C:18]([C:22](=[O:24])[CH3:23])=[C:19]([CH3:21])[CH:20]=2)=[CH:3][CH:4]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 75605N,N-Dimethylglycine hydrochlorideHCID 40573701-(4-Hydroxy-2,6-dimethylphenyl)ethanoneHCID 219958541-Bromo-4-(3-methoxypropoxy)benzene

Product 1

HCID 86690867HCID 86690867, compoundYield 21.1%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 1-bromo-4-isopropoxybenzene (21-2, 0.85 g, 3.9 mmol), 1-(4-hydroxy-2,6-dimethylphenyl)ethanone (4-2, 1.10 g, 6.71 mmol), N,N-dimethylglycine HCl salt (0.21 g, 1.5 mmol), copper iodide (0.12 g, 0.60 mmol), and cesium carbonate (2.90 g, 8.91 mmol) in dioxane (15.0 mL) was stirred at 120° C. for 48 h. The reaction mixture was cooled to room temperature, added with water, and extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous MgSO4, concentrated, and purified by flash column chromatography on silica gel (EtOAc:hexanes=1:5 as eluant) to give 1-{4-(4-(3-methoxypropoxy)phenoxy)-2,6-dimethylphenyl}ethanone (21-3, 0.27 g) as yellow oil in 21% yield: 1H NMR (CDCl3) δ 6.96 (dd, J=4.5, 2.2 Hz, 2 H), 6.89 (dd, J=4.3, 2.4 Hz, 2 H), 6.57 (s, 2 H), 4.05 (m, 2 H), 3.57 (t, J=6.2 Hz, 2H), 3.36 (s, 3 H), 2.66 (s, 3 H), 2.20 (s, 6 H), 2.05 (t, J=6.2 Hz, 2H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated
  6. custompurified by flash column chromatography on silica gel (EtOAc:hexanes=1:5 as eluant)

Sources & evidence

ORD record
ord-b112699f74ad4f6ea6208ddff5c4d61f
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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