Phenol → HCID 69409933, compound

HRID 853898Notes

Reaction equation

HRID 853898 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[C:10]([O:14][C:15]([N:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][C@H:18]1[CH2:26]OS(C1C=CC(C)=CC=1)(=O)=O)=[O:16])([CH3:13])([CH3:12])[CH3:11]>C1COCC1.CN(C=O)C.[Cl-].[Na+].O>[C:10]([O:14][C:15]([N:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][C@H:18]1[CH2:26][O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:16])([CH3:13])([CH3:11])[CH3:12]

Participants

7

Reactant 3

HCID 996PhenolHCID 24758Sodium hydrideHCID 10644859HCID 10644859, compound

Product 1

HCID 69409933HCID 69409933, compoundYield 74%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of phenol (1.715 g, 18.22 mmol, 1.2 eq) in THF (100 mL) was slowly added sodium hydride (0.915 g, 22.87 mmol, 1.5 eq) and the reaction was stirred at rt 1 hour. (S)-2-(Toluene-4-sulfonyloxymethyl)-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester (6.077 g, 15.14 mmol, 1 eq) (J. Org. Chem, 62, 7679, 1997) in THF (50 mL) and DMF (50 mL) were added and the mixture was heated at reflux overnight. After cooling, it was poured into brine and extracted with ethyl acetate. The combined organics were washed with brine, dried over magnesium sulfate and concentrated. The crude residue purified by column chromatography using ethyl acetate/hexanes (15/85) as an eluent to give the title compound as a colorless oil (3.371 g, 74%). NMR (400 Mz, DMSO-d6): consistent

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux overnight
  3. temperatureAfter cooling
  4. extractionextracted with ethyl acetate
  5. washThe combined organics were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe crude residue purified by column chromatography

Sources & evidence

ORD record
ord-2329a0a015ee4a27aceaaf22e5f57a53
Source dataset
uspto-grants-2007_08
Patent number
US07256198B2

Reaction notes

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