Potassium Hydroxide → 1-[4-(2-Hydroxyethoxy)phenyl]-2-(methylamino)ethanol

HRID 23711Notes

Reaction equation

HRID 23711 reaction equation
[Si]([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]2[O:22][C:21](=O)[N:20](C)[CH2:19]2)=[CH:14][CH:13]=1)(C(C)(C)C)(C)C.[OH-].[K+]>C(O)C>[OH:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]([OH:22])[CH2:19][NH:20][CH3:21])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 697404685-[4-(2-{[Tert-butyl(dimethyl)silyl]oxy}ethoxy)phenyl]-3-methyl-1,3-oxazolidin-2-one

Product 1

HCID 101490921-[4-(2-Hydroxyethoxy)phenyl]-2-(methylamino)ethanolYield 70.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-[4-(2-{[tert-butyl(dimethyl)silyl]oxy}ethoxy)phenyl]-3-methyl-1,3-oxazolidin-2-one (0.66 g, 1.87 mmol) and potassium hydroxide (4M aqueous solution, 1.4 mL, 5.61 mmol) dissolved in ethanol (8 mL) is refluxed for 2.5 h and then stirred at room temperature for 16 h. Reaction mixture is concentrated under reduced pressure, water (5 mL) is added and the mixture is extracted with chloroform:methanol (9:1) (5×10 mL). The combined organic layers are dried over magnesium sulfate and concentrated to provide a residual oil. This oil is triturated with ether to provide a white solid (0.28 g).

Workup

  1. temperatureis refluxed for 2.5 h
  2. customReaction mixture
  3. concentrationis concentrated under reduced pressure, water (5 mL)
  4. additionis added
  5. extractionthe mixture is extracted with chloroform:methanol (9:1) (5×10 mL)
  6. dry with materialThe combined organic layers are dried over magnesium sulfate
  7. concentrationconcentrated
  8. customto provide a residual oil
  9. customThis oil is triturated with ether

Sources & evidence

ORD record
ord-b148a1b29d02402faf49d895fa4968de
Source dataset
uspto-grants-2005_02
Patent number
US06852731B2

Reaction notes

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