Trimethyl orthoformate → HCID 21886104, compound

HRID 1686140Notes

Reaction equation

HRID 1686140 reaction equation
[Br:1][C:2]1[CH:9]=[C:6](C=O)[C:5]([OH:10])=[CH:4][CH:3]=1.CO[CH:13]([O:16][CH3:17])[O:14][CH3:15].CC1C=CC(S(O)(=O)=O)=CC=1.O.C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])O.[Na+]>CO.[Cl-].[Na+].O>[Br:1][C:2]1[CH:9]=[CH:6][C:5]([OH:10])=[C:4]([CH:13]([O:14][CH3:15])[O:16][CH3:17])[CH:3]=1

Participants

8

Reactant 5

HCID 9005Trimethyl orthoformateHCID 11430Potassium CarbonateHCID 728635-BromosalicylaldehydeHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 21886104HCID 21886104, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 5-bromosalicylaldehyde (4.00 g, 19.90 mmol) in methanol (50 ml) were added orthoformic acid trimethyl (9.70 g, 10.00 ml, 91.41 mmol) and TsOH.H2O (38.04 mg, 0.20 mmol), followed by reacting them at room temperature for 1 hour. Following neutralization with potassium carbonate (55.28 mg, 0.40 mmol), the solution was cleansed with brine and 5%-sodium hydrogen carbonate (=1:1, 50 ml) and extracted with pet ether (×2). A pool of the organic layer thus formed was dried over anhydrous MgSO4 and filtered. The filtrate was concentrated in a vacuum to prepare the object compound (white, solid, 4.92 g, 100%).

Workup

  1. customat room temperature
  2. customfor 1 hour
  3. extractionextracted with pet ether (×2)
  4. customA pool of the organic layer thus formed
  5. dry with materialwas dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in a vacuum
  8. customto prepare the object compound (white, solid, 4.92 g, 100%)

Sources & evidence

ORD record
ord-a9b5de647ecb4a8bac19260e69f54857
Source dataset
uspto-grants-2012_04
Patent number
US08148541B2

Reaction notes

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