Chlorotrimethylsilane → HCID 59410091, compound

HRID 2404856Notes

Reaction equation

HRID 2404856 reaction equation
[N+:1]([O-:4])([O-])=[O:2].[K+].C[Si](Cl)(C)C.[C:11](=[O:27])([O:25][CH3:26])[O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH3:20])=[CH:15][C:14]=1[C:21]([CH3:24])([CH3:23])[CH3:22].[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl>[C:11](=[O:27])([O:25][CH3:26])[O:12][C:13]1[CH:18]=[C:17]([N+:1]([O-:4])=[O:2])[C:16]([CH2:19][CH3:20])=[CH:15][C:14]=1[C:21]([CH3:22])([CH3:23])[CH3:24]

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 24434Potassium NitrateHCID 6451240Aluminum(III) ChlorideHCID 59410128HCID 59410128, compound

Product 1

HCID 59410091HCID 59410091, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of KNO3 (3.9 g, 38.57 mmol) in DCM (50 mL) was added TMSCl (5.5 g, 50.62 mmol) and 2-tert-butyl-4-ethylphenyl methyl carbonate (6 g, 25.39 mmol) at 0° C. After stirring for 15 minutes, AlCl3 (10 g, 0.08 mol) was added and then the reaction mixture was stirred for 2 h. The reaction mixture was poured onto ice water and extracted with EtOAc (50 mL×3). The combined organic layers were dried over anhydrous Na2SO4, filtered and evaporated under vacuum to give the crude compound, which was purified by silica gel column chromatography (10-15% EtOAc in petroleum ether as eluant) to yield 2-tert-butyl-4-ethyl-5-nitrophenyl methyl carbonate (5 g, 70%). 1H NMR (400 MHz, CDCl3) 7.69 (s, 1H), 7.25 (s, 1H), 3.82 (s, 3H), 2.54 (q, J=7.6 Hz, 2H), 1.26 (s, 9H), 1.15 (d, J=7.6 Hz, 3H).

Workup

  1. stirringthe reaction mixture was stirred for 2 h
  2. additionThe reaction mixture was poured onto ice water
  3. extractionextracted with EtOAc (50 mL×3)
  4. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated under vacuum
  7. customto give the crude compound, which
  8. customwas purified by silica gel column chromatography (10-15% EtOAc in petroleum ether as eluant)

Sources & evidence

ORD record
ord-2d3f822fc5744bed8aeea56e55d9d537
Source dataset
uspto-grants-2014_08
Patent number
US08802700B2

Reaction notes

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