Phenol → (2R)-2-(Phenoxymethyl)oxirane

HRID 20375

Reaction equation

HRID 20375 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[O:10]1[CH2:12][C@@H:11]1[CH2:13]OS(C1C=CC=C([N+]([O-])=O)C=1)(=O)=O>CN(C)C=O>[O:7]([CH2:13][C@H:11]1[CH2:12][O:10]1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 24758Sodium hydrideHCID 146513Benzenesulfonic acid, 3-nitro-, (2R)-2-oxiranylmethyl ester

Product 1

HCID 1534344(2R)-2-(Phenoxymethyl)oxiraneYield 81.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Add phenol (1.089 g, 11.572 mmol) to a slurry of sodium hydride (0.347 g, 14.465 mmol) in N,N-dimethylformamide (77.1 mL) and stir at room temperature for 40 minutes. Add 3-nitrobenzenesulfonic acid (R)-1-oxiranylmethyl ester (3.00 g, 11.572 mmol) and stir at room temperature for 16 hours (J. Org. Chem., 54, 1296-1304 (1989). Quench with saturated aqueous ammonium chloride (75 mL), dilute with water (75 mL) and extract with diethyl ether (3×300 mL). Combine the organic extracts, wash with saturated aqueous sodium bicarbonate (200 mL), saturated aqueous ammonium chloride (200 mL), dry (magnesium sulfate), filter and purify (silica gel chromatography, eluting with 10:90 to 50:50 ethyl acetate:hexanes) to give the desired compound as a clear liquid (1.410 g, 81.1%).

Workup

  1. customQuench with saturated aqueous ammonium chloride (75 mL)
  2. additiondilute with water (75 mL)
  3. extractionextract with diethyl ether (3×300 mL)
  4. washCombine the organic extracts, wash with saturated aqueous sodium bicarbonate (200 mL), saturated aqueous ammonium chloride (200 mL)
  5. dry with materialdry (magnesium sulfate)
  6. filtrationfilter
  7. custompurify
  8. wash(silica gel chromatography, eluting with 10:90 to 50:50 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-dcce78decbd644babd0ddb737e71f34b
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Linked notes

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