Cesium carbonate → 2-({2-[(4-{[3-Methyl-6-(methyloxy)-2-phenyl-1-naphthalenyl]oxy}phenyl)oxy]ethyl}oxy)ethanol

HRID 1993014Notes

Reaction equation

HRID 1993014 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+].Cl[CH2:35][CH2:36][O:37][CH2:38][CH2:39][OH:40]>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][O:37][CH2:38][CH2:39][OH:40])=[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 123612-(Chloroethoxy)ethanolHCID 685394164-{[3-Methyl-6-(methyloxy)-2-phenyl-1-naphthalenyl]oxy}phenol

Product 1

HCID 116622532-({2-[(4-{[3-Methyl-6-(methyloxy)-2-phenyl-1-naphthalenyl]oxy}phenyl)oxy]ethyl}oxy)ethanolYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The O-alkylation procedure described for Example 63 (Step 2) was employed with 4-{[3-methyl-6-(methyloxy)-2-phenyl-1-naphthalenyl]oxy}phenol (233) (0.605 g, 1.697 mmol), Cs2CO3 (1.658 g, 5.09 mmol), anhydrous DMF (8 mL), and 2-[(2-chloroethyl)oxy]ethanol (0.604 mL, 8.49 mmol) under N2. The reaction mixture was refluxed for 15 h and then cooled to room temperature. Standard work-up followed by column chromatography gave 0.754 g (˜100%) of the title compound (290) as a colorless oil. 1H NMR (400 MHz, DMSO-d6): δ 7.65 (s, 1H), 7.58 (d, J=8.8 Hz, 1H), 7.31 (d, J=2.4 Hz, 1H), 7.29 (d, J=7.6 Hz, 2H), 7.24 (m, 1H), 7.16 (d, J=8.4 Hz, 2H), 7.05 and 7.03 (dd, J1=9.2 Hz, J2=2.4 Hz, 1H), 6.67 (d, J=9.2 Hz, 2H), 6.47 (d, J=9.2 Hz, 2H), 4.58 (t, J=5.6 Hz, 1H), 3.91 (t, J=4.8 Hz, 2H), 3.85 (s, 3H), 3.63 (t, J=4.8 Hz, 2H), 3.45 (t, J=5.2 Hz, 2H), 3.43 (t, J=4.4 Hz, 2H), 2.17 (s, 3H). LCMS (ESI) m/z 445.27 (M+H)+.

Workup

  1. temperatureThe reaction mixture was refluxed for 15 h

Sources & evidence

ORD record
ord-12df0120d2124e178872ae7c38233317
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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