Styrene Oxide → HCID 58306818, compound

HRID 1909876Notes

Reaction equation

HRID 1909876 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2.CN1CCCN(C)C1=O.[C:20]1([CH:26]2[CH2:28][O:27]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:28][CH:26]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[OH:27])[CH:8]=[CH:7]2

Participants

7

Reactant 4

HCID 7276Styrene OxideHCID 10796Cesium carbonateHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 27570207-Bromoindole

Product 1

HCID 58306818HCID 58306818, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 7-bromoindole (3.3 g) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone (33 mL) were added 2-phenyloxirane (2.5 mL) and cesium carbonate (11 g) at room temperature, followed by stirring at 80° C. for 12 hours. To the reaction mixture were added ethyl acetate and water, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to obtain 2-(7-bromo-1H-indol-1-yl)-1-phenylethanol (5.1 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-0dd1b04a7d144ea680216a680f646d68
Source dataset
uspto-grants-2013_12
Patent number
US08598355B2

Reaction notes

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