2-Nitrobenzaldehyde → HCID 11448149, compound

HRID 1097771Notes

Reaction equation

HRID 1097771 reaction equation
[CH3:1][O:2][C:3]([O:7][Si](C)(C)C)=[C:4]([CH3:6])[CH3:5].[N+:12]([C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[CH:17]=[O:18])([O-:14])=[O:13]>C(Cl)Cl.FC(F)(F)S([O-])(=O)=O.[Sc+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O>[CH3:1][O:2][C:3](=[O:7])[C:4]([CH3:6])([CH3:5])[CH:17]([OH:18])[C:16]1[CH:19]=[CH:20][CH:21]=[CH:22][C:15]=1[N+:12]([O-:14])=[O:13]

Participants

5

Reactant 2

HCID 111012-NitrobenzaldehydeHCID 552336Silane, ((1-methoxy-2-methyl-1-propenyl)oxy)trimethyl-

Product 1

HCID 11448149HCID 11448149, compoundYield 31.6%

Reagents, catalysts & solvents 2

HCID 2734571Scandium(III) triflateCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1-Methoxy-1-(trimethylsiloxy)-2-methyl-1-propene (2.4 mL, 2.092 g, 12 mmol) is added dropwise to a suspension of 2-Nitro-benzaldehyde (1.51 g, 10 mmol), Scandium (III) trifluoromethanesulfonate (148 mg, 0.3 mmol) in 30 mL of dry CH2Cl2 at −78° C. The resulting mixture is slowly warmed up to 0° C. and stirred for 1 h. The reaction is quenched with 1 M HCl and stirred for 1 h at room temperature. After extraction with ethyl acetate (20 mL×3), washed with brine, dried over anhydrous Na2SO4 and concentration, the residue is purified by flash column, and gives a yellow oil (800 mg).

Workup

  1. customThe reaction is quenched with 1 M HCl
  2. stirringstirred for 1 h at room temperature
  3. extractionAfter extraction with ethyl acetate (20 mL×3)
  4. washwashed with brine
  5. dry with materialdried over anhydrous Na2SO4 and concentration
  6. customthe residue is purified by flash column

Sources & evidence

ORD record
ord-1a923df498ff4f5f9d667ac818b852fd
Source dataset
uspto-grants-2012_03
Patent number
US08143278B2

Reaction notes

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