Ethyl Acetate → 2-Trimethylsilanylethyl (3-benzyloxy-4-nitrophenoxy)acetate

HRID 660760Notes

Reaction equation

HRID 660760 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH2:7][Si:8]([CH3:11])([CH3:10])[CH3:9])=[O:4].[CH2:12]([O:19][C:20]1[CH:21]=[C:22]([OH:29])[CH:23]=[CH:24][C:25]=1[N+:26]([O-:28])=[O:27])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].CCOC(C)=O>CN(C=O)C>[CH2:12]([O:19][C:20]1[CH:21]=[C:22]([CH:23]=[CH:24][C:25]=1[N+:26]([O-:28])=[O:27])[O:29][CH2:2][C:3]([O:5][CH2:6][CH2:7][Si:8]([CH3:11])([CH3:10])[CH3:9])=[O:4])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 109777113-(Benzyloxy)-4-nitrophenolHCID 127231772-(Trimethylsilyl)ethyl bromoacetate

Product 1

HCID 866325882-Trimethylsilanylethyl (3-benzyloxy-4-nitrophenoxy)acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-trimethylsilylethyl bromoacetate (J. Org. Chem. 51, 1537 (1986) (13.72 g, 56.0 mmol), 3-benzyloxy-4-nitrophenol (EP application 095121) (13.38 g, 55.9 mmol), and potassium carbonate (15.46 g, 112 mmol) in DMF (40 mL) is stirred at RT for 18 h. The mixture is poured into EtOAc and extracted once with water and five times with brine. The organic layer is dried, filtered, and concentrated to afford the title compound as a pale brown liquid: 1H NMR (CDCl3)δ 7.93 (d, J=9.1 Hz, 1H), 7.42 (d, J=7.1 Hz, 2H), 7.34 (t, J=7.1 Hz, 2H), 7.28 (t, J=7.1 Hz, 1H), 6.60 (d, J=2.5 Hz, 1H), 6.41 (dd, J=9.1, 2.5 Hz, 1H), 5.15 (s, 2H), 4.57 (s, 2H), 4.25 (m, 2H), 0.97 (m, 2H), 0.00 (s, 9H).

Workup

  1. extractionextracted once with water and five times with brine
  2. customThe organic layer is dried
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b0b432a92bf94534b1ac549d737ddff7
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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