Phenol → HCID 24964144, compound

HRID 1160204Notes

Reaction equation

HRID 1160204 reaction equation
Br[CH2:2][C:3]1[CH:21]=[CH:20][C:6]([CH2:7][N:8]2[CH2:12][C@@H:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[O:10][C:9]2=[O:19])=[CH:5][CH:4]=1.[C:22]1([OH:28])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>O.CC(=O)CC>[O:28]([CH2:2][C:3]1[CH:21]=[CH:20][C:6]([CH2:7][N:8]2[CH2:12][C@@H:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[O:10][C:9]2=[O:19])=[CH:5][CH:4]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 996PhenolHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 24963437HCID 24963437, compound

Product 1

HCID 24964144HCID 24964144, compoundYield 71.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 3-(4-bromomethyl-benzyl)-5-(R)-phenyl-oxazolidin-2-one (30 mg, 0.086 mmol, prepared according to procedure 4), phenol (10 mg, 0.1 mmol), potassium carbonate (25 mg, 0.18 mmol), potassium iodide (3 mg, 0.008 mmol) and 2-butanone was heated at 80° C. overnight. The reaction mixture was allowed to cool down to RT, mixed with water (5 mL), organic phase was separated and the aq. phase was extracted with ethyl acetate (3×8 mL). The combined organic phase was washed with brine (5 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to get the product. Purification by chromatography on silica gel, eluting with 5-20% ethyl acetate in hexanes yielded the title compound (22 mg, 59%) as a white solid. 1H NMR (300 MHz, CDCl3): δ 7.38 (m, 11H), 6.99 (m, 3H), 5.50 (t, 1H), 5.08 (s, 2H), 4.59 (d, 1H), 4.44 (d, 1H), 3.80 (m, 1H), 3.34 (m, 1H).

Workup

  1. temperatureto cool down to RT
  2. customwas separated
  3. extractionthe aq. phase was extracted with ethyl acetate (3×8 mL)
  4. washThe combined organic phase was washed with brine (5 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto get the product
  8. customPurification by chromatography on silica gel
  9. washeluting with 5-20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-19a31aa492e94480ac16d96fd494af66
Source dataset
uspto-grants-2010_10
Patent number
US07816354B2

Reaction notes

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