(3-Benzyloxy-4-nitrophenoxy)-tert-butyldimethylsilane → 2-Benzyloxy-4-(tert-butyldimethylsilanyloxy)-phenylamine

HRID 660510Notes

Reaction equation

HRID 660510 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:20]=[CH:21][C:22]=1[N+:23]([O-])=O)[O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CCOC(C)=O.[Pt]>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([O:12][Si:13]([C:16]([CH3:18])([CH3:17])[CH3:19])([CH3:14])[CH3:15])[CH:20]=[CH:21][C:22]=1[NH2:23])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 68839042(3-Benzyloxy-4-nitrophenoxy)-tert-butyldimethylsilane

Product 1

HCID 688401272-Benzyloxy-4-(tert-butyldimethylsilanyloxy)-phenylamine

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (3-benzyloxy-4-nitrophenoxy)-tert-butyldimethylsilane in EtOAc (50 mL) is hydrogenated over 5% Pt/C (630 mg) at 1 atm for 18 h. The catalyst is filtered off through Celite and the solvent removed under reduced pressure to afford the title compound as an oil: 1H NMR (CDCl3δ7.26 (m, 5H), 6.48 (d, J=8.3 Hz, 1H), 6.29 (d, J=2.5 Hz, 1H), 6.19 (dd, J=8.3, 2.5 Hz, 1H), 4.93 (s, 2H), 0.83 (s, 9H), 0.00 (s, 6H); (M+1)+=330.

Workup

  1. filtrationThe catalyst is filtered off through Celite
  2. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-0aefd8027cbb4739b09e3741f7395d3b
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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