Methyl morpholine oxide → HCID 57493914, compound

HRID 2280608Notes

Reaction equation

HRID 2280608 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-62124bb8ca6c4469b15c1600116089bc
Source dataset
uspto-grants-2015_09
Patent number
US09139536B2

Reaction notes

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