Ethanol → HCID 22722681, compound

HRID 442903Notes

Reaction equation

HRID 442903 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([NH:16]C(=O)C(O)(C)C)[CH:12]=[C:13]([CH3:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].C(O)C>O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:12]=[C:13]([CH3:15])[CH:14]=1)[NH2:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 54415131HCID 54415131, compound

Product 1

HCID 22722681HCID 22722681, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-(3-Benzyloxy-5-methylphenyl)-2-hydroxy-2-methylpropanamide (600 mg, 2.0 mmol), as prepared in the preceding step, was mixed with 10N NaOH (25 mL) and ethanol (10 mL), and the mixture was refluxed for 2 days. After cooling to ambient temperature, the mixture was diluted with water (60 mL) and extracted with dichloromethane (3×60 mL). The dichloromethane solution was washed with brine (2×50 mL) and dried over Na2SO4. After evaporating the solvent in vacuo, the residue was purified by flash column chromatography (dichloromethane) to give the title compound as a yellow oil (265 mg, 61%). 1H-NMR (300 MHz, CDCl3) δ 7.37 (m, 5 H), 6.24 (s, 1 H), 6.14 (s, 2 H), 5.00 (s, 2 H), 3.59 (br s, 2 H), 2.23 (s, 3 H).

Workup

  1. temperaturethe mixture was refluxed for 2 days
  2. extractionextracted with dichloromethane (3×60 mL)
  3. washThe dichloromethane solution was washed with brine (2×50 mL)
  4. dry with materialdried over Na2SO4
  5. customAfter evaporating the solvent in vacuo
  6. customthe residue was purified by flash column chromatography (dichloromethane)

Sources & evidence

ORD record
ord-d2f65d561f874f45b7e98e272fb0ae56
Source dataset
uspto-grants-1999_04
Patent number
US05891909

Reaction notes

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