HCID 86724349, compound → HCID 86724350, compound

HRID 1482696Notes

Reaction equation

HRID 1482696 reaction equation
[C:1]([Si:5]([CH3:20])([CH3:19])[O:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[Si:5]([O:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=1)([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:20])[CH3:19]

Participants

4

Reactant 1

HCID 86724349HCID 86724349, compound

Product 1

HCID 86724350HCID 86724350, compoundYield 91.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a suspension of Pd/C (2.5 g) in methanol (30 mL), in a 100 mL 3-neck RBF, was added tert-butyldimethyl(2-(4-nitrophenoxy)ethoxy)silane (5.0 g) under a nitrogen atmosphere at room temperature. Hydrogen gas was bubbled through the reaction for 3 hr at room temperature. The reaction was monitored on TLC using ethyl acetate:hexane (3:7) as mobile phase. After completion, the reaction mixture was filtered using Celite and the filter cake was washed with methanol. The filtrate was concentrated under reduced pressure at 40° C. to give 4.12 g of 4-(2-((tert-butyldimethylsilyl)oxy)ethoxy)aniline as a brown liquid. M+1=309.2.

Workup

  1. customHydrogen gas was bubbled through the reaction for 3 hr at room temperature
  2. filtrationAfter completion, the reaction mixture was filtered
  3. washthe filter cake was washed with methanol
  4. concentrationThe filtrate was concentrated under reduced pressure at 40° C.

Sources & evidence

ORD record
ord-7e1ecace410c409a8e6e079187faa9dd
Source dataset
uspto-grants-2016_08
Patent number
US09415049B2

Reaction notes

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