Triethylsilane → HCID 89814959, compound

HRID 1487149Notes

Reaction equation

HRID 1487149 reaction equation
[CH3:1][C:2]([O:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-])=O)[CH:9]=1)([CH3:6])[C:3]([NH2:5])=[O:4].C([SiH](CC)CC)C>CO.[Pd]>[NH2:14][C:10]1[CH:9]=[C:8]([CH:13]=[CH:12][CH:11]=1)[O:7][C:2]([CH3:6])([CH3:1])[C:3]([NH2:5])=[O:4]

Participants

5

Reactant 2

HCID 12052TriethylsilaneHCID 82040968HCID 82040968, compound

Product 1

HCID 89814959HCID 89814959, compoundYield 65.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of 2-methyl-2-(3-nitrophenoxy)propanamide (0.910 g, 4.06 mmol) in MeOH (15 ml) was added Pd—C (10%, 0.346 g) and triethylsilane (6.48 ml, 40.6 mmol) (slow addition) at room temperature. The reaction mixture was stirred at same temperature for 30 min. and filtered through celite, washed with methanol (50 ml). The Filtrate was concentrated under vacuum to get the crude compound. The crude compound was purified by flash chromatography to give the title product (0.516 g).

Workup

  1. filtrationfiltered through celite
  2. washwashed with methanol (50 ml)
  3. concentrationThe Filtrate was concentrated under vacuum
  4. customto get the crude compound
  5. customThe crude compound was purified by flash chromatography

Sources & evidence

ORD record
ord-19b042979a3b41ec8f49510ad59732d2
Source dataset
uspto-grants-2016_08
Patent number
US09428499B2

Reaction notes

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