Phenol → (2S)-2-(phenoxymethyl)oxirane

HRID 1370195Notes

Reaction equation

HRID 1370195 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:8]1[O:10][C@@H:9]1[CH2:11]OS(C1C=C([N+]([O-])=O)C=CC=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[O:7]([CH2:11][C@@H:9]1[CH2:8][O:10]1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl ester

Product 1

HCID 1534345(2S)-2-(phenoxymethyl)oxiraneYield 99.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of phenol (9.4 g, 100 mmol) and (2S)-(+)glycidyl 3-nitrobenzenesulfonate(25.9 g, 100 mmol) in 500 mL of acetone was treated with 3 equivalents of potassium carbonate (41.5 g, 300 mmol) and stirred at reflux for 1 day. The suspension was cooled to ambient temperature; the solid was filtered; and the filtrate concentrated to dryness. The residue was partitioned between methylene chloride and water and the aqueous layer was extracted with methylene chloride. The organic layers were combined and dried over magnesium sulfate and concentrated to give the title compound (15.0 g, 99%) as an orange oil; 1H NMR (300 MHz, CDCl3) δ 2.76 (dd, J=4.9, 2.6 Hz, 1 H), 2.90 (dd, J=4.9, 4.9 Hz, 1 H), 3.30-3.40 (m, 1 H), 3.95 (dd, J=11.0, 5.4 Hz, 1 H), 4.18 (dd, J=11.0, 3.0 Hz, 1 H), 6.85-7.00 (m, 3H), 7.25-7.35 (m, 2H); MS (ES) m/z: 151.0 (MH+).

Workup

  1. temperatureat reflux for 1 day
  2. filtrationthe solid was filtered
  3. concentrationand the filtrate concentrated to dryness
  4. customThe residue was partitioned between methylene chloride and water
  5. extractionthe aqueous layer was extracted with methylene chloride
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-19827d4c21724414a5d0f36c4951614a
Source dataset
uspto-grants-2003_06
Patent number
US06583140B2

Reaction notes

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