4-Ethoxyaniline → HCID 67131106, compound

HRID 527963Notes

Reaction equation

HRID 527963 reaction equation
[CH2:1]([O:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)[CH3:2].[C:11]([Si:15]([CH3:23])([CH3:22])[O:16][CH2:17][CH2:18][C@@H:19]1[CH2:21][O:20]1)([CH3:14])([CH3:13])[CH3:12]>CCO.O>[C:11]([Si:15]([CH3:23])([CH3:22])[O:16][CH2:17][CH2:18][C@@H:19]([OH:20])[CH2:21][NH:8][C:7]1[CH:9]=[CH:10][C:4]([O:3][CH2:1][CH3:2])=[CH:5][CH:6]=1)([CH3:12])([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 90764-EthoxyanilineHCID 11217932HCID 11217932, compound

Product 1

HCID 67131106HCID 67131106, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 4-ethoxy-aniline (commercial; 3.2 mL) in EtOH/water (9:1; 150 mL) was reacted with (2R)-2-[2-[[(tert-butyl)dimethylsilyl]oxy]ethyl]-oxirane (prepared according to WO 2007/144423) and further heated at 80° C. overnight. The solvents were removed under reduced pressure and the residue was purified by CC (EA/Hept 1:1), affording a brown oil (5.22 g; 62% yield).

Workup

  1. customThe solvents were removed under reduced pressure
  2. customthe residue was purified by CC (EA/Hept 1:1)
  3. customaffording a brown oil (5.22 g; 62% yield)

Sources & evidence

ORD record
ord-10cc7cb9e74045e09d9846e677f7465d
Source dataset
uspto-grants-2016_05
Patent number
US09346804B2

Reaction notes

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