Potassium Carbonate → Ethyl 4-({4-[(4-fluorophenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl}oxy)butanoate

HRID 2241030Notes

Reaction equation

HRID 2241030 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+].Br[CH2:33][CH2:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37]>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][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:11][CH:10]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 111635614-[(4-Fluorophenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenol

Product 1

HCID 68506769Ethyl 4-({4-[(4-fluorophenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl}oxy)butanoateYield 90.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The o-alkylation procedure described for 10 (example 5, step 2) was used. To a stirred suspension of 4-[(4-fluorophenyl)(3,3,5,5 tetramethylcyclohexylidene) methyl]phenol 9 (0.590 g, 1.74 mmol), K2CO3 (0.482 g, 3.5 mmol), and acetone (50 mL) was added ethyl 4-bromobutyrate (0.62 mL, 4.4 mmol) under a nitrogen atmosphere at RT. The reaction mixture was refluxed for 6 h, cooled to RT and filtered. Standard work-up followed by purification afforded 0.712 g (90%) of compound 12 as a white foam. 1H NMR (300 MHz, CDCl3): δ 7.14 (d, J=5.7 Hz, 1H), 7.11 (d, J=5.7 Hz, 1H), 7.07 (d, J=8.7 Hz, 2H), 6.98 and 6.95 (dd, J=8.7 Hz, J2=8.7 Hz, 2H), 6.81 (d, J=8.4 Hz, 2H), 4.16 (q, J=7.2 Hz, 2H), 3.99 (t, J=6.00 Hz, 2H), 3.49 (t, J=6.3 Hz, 2H), m, 2H), 2.11 (quint., J=6.30 Hz, 2H), 2.00 (s, 2H), 1.96 (s, 2H), 1.31 (br s, 2H), 1.27 (t, J=7.2 Hz, 3H), 0.95 (s, 6H), 0.94 (s, 6H). LCMS (ESI): m/z 475 (M+Na)+.

Workup

  1. temperatureThe reaction mixture was refluxed for 6 h
  2. filtrationfiltered
  3. customStandard work-up followed by purification

Sources & evidence

ORD record
ord-eb5e8e9d490a4cafbdee0e3f7f4c2ad9
Source dataset
uspto-grants-2010_05
Patent number
US07723393B2

Reaction notes

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