Potassium Carbonate → HCID 66817482, compound

HRID 1754936Notes

Reaction equation

HRID 1754936 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[CH3:10].C1(C)C=CC(S(O[CH2:21][C@H:22]2[CH2:26][O:25][C:24]([CH3:28])([CH3:27])[O:23]2)(=O)=O)=CC=1.C([O-])([O-])=O.[K+].[K+]>CN(C)C=O.CCOC(C)=O>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([O:9][CH2:21][C@H:22]2[CH2:26][O:25][C:24]([CH3:28])([CH3:27])[O:23]2)=[CH:4][C:3]=1[CH3:10]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 819704-Bromo-3,5-dimethylphenolHCID 6993835(R)-(-)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-Toluenesulfonate

Product 1

HCID 66817482HCID 66817482, compoundYield 95.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-bromo-3,5-dimethyl-phenol (500 mg, 2.49 mmol), (R)-(−)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate (856 mg, 2.99 mmol) and K2CO3 (1.03 g, 7.45 mmol) in dimethylformamide (5 ml) was stirred at 100° C. for two hours. The reaction mixture was diluted with AcOEt, and the organic layer was then washed with water (×2), dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (AcOEt-hexane) to give (S)-4-(4-bromo-3,5-dimethyl-phenoxymethyl)-2,2-dimethyl-[1,3]dioxolane as a colorless solid (749 mg, 95%).

Workup

  1. washthe organic layer was then washed with water (×2)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (AcOEt-hexane)

Sources & evidence

ORD record
ord-60c748536da34e0688c40f60b44ec6af
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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