Potassium Carbonate → 2-{[2-({4-[(4-Fluorophenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl}oxy)ethyl]oxy}ethanol

HRID 2241042Notes

Reaction equation

HRID 2241042 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[C:16]2[CH2:21][C:20]([CH3:23])([CH3:22])[CH2:19][C:18]([CH3:25])([CH3:24])[CH2:17]2)[C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:33][CH2:34][O:35][CH2:36][CH2:37][OH:38]>CC(C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[C:16]2[CH2:17][C:18]([CH3:25])([CH3:24])[CH2:19][C:20]([CH3:23])([CH3:22])[CH2:21]2)[C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:33][CH2:34][O:35][CH2:36][CH2:37][OH:38])=[CH:11][CH:10]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123612-(Chloroethoxy)ethanolHCID 111635614-[(4-Fluorophenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenol

Product 1

HCID 119925682-{[2-({4-[(4-Fluorophenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl}oxy)ethyl]oxy}ethanolYield 45%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The O-alkylation procedure described for 10 (Example 5, step 2) was followed using 9 (339 mg, 1 mmol), K2CO3 (414 mg, 3 mmol), 2-[(2-chloroethyl)oxy]ethanol (0.63 mL, 6 mmol), and acetone (30 mL). The reaction mixture was refluxed for 60 h. The reaction mixture was filtered, concentrated, and purified by column chromatography to give 190 mg (45%) of the title product 24 as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 7.16-7.13 (m, 2H), 7.11-7.07 (m, 2H), 7.0 (d, J=8.4 Hz, 2H), 6.84 (d, J=8.4 Hz, 2H), 4.59 (t, J=5.2 Hz, 2H), 4.03 (t, J=4.8 Hz, 2H), 3.70 (t, J=4.4 Hz, 2H), 3.49-3.44 (m, 4H), 1.90 (s, 2H), 1.86 (s, 2H), 1.24 (s, 2H), 0.87 (s, 6H), 0.87 (s, 6H). LCMS (APCI): m/z 427 (M+H)+.

Workup

  1. temperatureThe reaction mixture was refluxed for 60 h
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-f0f48ad5c30b45c4848222ea49713c95
Source dataset
uspto-grants-2010_05
Patent number
US07723393B2

Reaction notes

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