Potassium Carbonate → 1-(4-{1-Ethyl-1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenoxy)-3,3-dimethyl-butan-2-one

HRID 547067Notes

Reaction equation

HRID 547067 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][C:8]([C:11]([CH2:13]Cl)=[O:12])([CH3:10])[CH3:9].[CH2:15]([C:17]([C:35]1[CH:40]=[CH:39][C:38]([OH:41])=[C:37]([CH3:42])[CH:36]=1)([C:20]1[CH:25]=[CH:24][C:23]([B:26]2[O:30][C:29]([CH3:32])([CH3:31])[C:28]([CH3:34])([CH3:33])[O:27]2)=[CH:22][CH:21]=1)[CH2:18][CH3:19])[CH3:16].C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH2:15]([C:17]([C:35]1[CH:40]=[CH:39][C:38]([O:41][CH2:13][C:11](=[O:12])[C:8]([CH3:10])([CH3:9])[CH3:7])=[C:37]([CH3:42])[CH:36]=1)([C:20]1[CH:25]=[CH:24][C:23]([B:26]2[O:27][C:28]([CH3:33])([CH3:34])[C:29]([CH3:31])([CH3:32])[O:30]2)=[CH:22][CH:21]=1)[CH2:18][CH3:19])[CH3:16]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 835721-ChloropinacoloneHCID 516892Sodium BicarbonateHCID 574435234-{1-Ethyl-1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenol

Product 1

HCID 574435241-(4-{1-Ethyl-1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenoxy)-3,3-dimethyl-butan-2-oneYield 32%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

Potassium carbonate (54.5 mg, 0.395 mmol) and 1-chloropinacolin (71 mg, 0.526 mmol) were added to a solution of 4-{1-ethyl-1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenol (Example 143-(3); 100 mg, 0.263 mmol) in N,N-dimethylformamide (2 mL), and the mixture was stirred with microwave heating at 140° C. for 15 minutes. The reaction mixture was then poured into a saturated aqueous sodium bicarbonate solution, followed by extraction with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=100:0 to 50:50, 40 minutes) to give the target compound as a colorless oil (39.7 mg, 32%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=100:0 to 50:50, 40 minutes)

Sources & evidence

ORD record
ord-b1b2032ffc654c0f97465a4e91084aa7
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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