Methyl morpholine oxide → HCID 57493914, compound

HRID 508350Notes

Reaction equation

HRID 508350 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.C[N+:13]1([O-])[CH2:18]COCC1.[CH3:20][Si:21](C#N)([CH3:23])[CH3:22]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7]([O:11][Si:21]([CH3:23])([CH3:22])[CH3:20])([C:18]#[N:13])[CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 82029Methyl morpholine oxideHCID 82115Trimethylsilyl cyanideHCID 5206955-Bromo-1-indanone

Product 1

HCID 57493914HCID 57493914, compoundYield 286.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-bromo-2,3-dihydro-1H-inden-1-one (10.0 g, 47.4 mmol) and N-methyl-morpholine N-oxide (1.67 g, 14.21 mmol) in CH2Cl2 (50 ml) was added trimethylsilylcyanide (7.05 g, 71.1 mmol), and the resultant solution was stirred at room temperature for 72 h, and then concentrated in vacuo. The crude product was purified by column chromatography on silica gel using 5% EtOAc in hexanes as the eluent to give the title compound as a colorless liquid (12.65 g, 86%).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe crude product was purified by column chromatography on silica gel using 5% EtOAc in hexanes as the eluent

Sources & evidence

ORD record
ord-aa8e3ced3d444db48860190da08378e0
Source dataset
uspto-grants-2015_08
Patent number
US09095590B2

Reaction notes

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