Trimethyl orthoformate → HCID 23155413, compound

HRID 2080813Notes

Reaction equation

HRID 2080813 reaction equation
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1)=O.[CH2:11]([O:13][CH:14]([O:19][CH2:20][CH3:21])[CH2:15][CH2:16][CH2:17][NH2:18])[CH3:12].C(OC)(OC)OC.[BH4-].[Na+]>CO>[CH2:20]([O:19][CH:14]([O:13][CH2:11][CH3:12])[CH2:15][CH2:16][CH2:17][NH:18][CH2:1][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1)[CH3:21]

Participants

6

Reactant 4

HCID 9005Trimethyl orthoformateHCID 660424-CyanobenzaldehydeHCID 806724,4-DiethoxybutylamineHCID 4311764Sodium borohydride

Product 1

HCID 23155413HCID 23155413, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Formylbenzonitrile (612.0 mg) was dissolved in methanol (18.4 ml), and 4,4-diethoxybutylamine (752.5 mg) and trimethyl orthoformate (1.53 ml) were added thereto. The whole was stirred at room temperature for 18 hours. Subsequently, the solution was added with sodium borohydride (529.7 mg) under ice-cooling and stirred at room temperature for additional 30 minutes. The reaction solution was concentrated under reduced pressure. The residue was added with water and the whole was subjected to extraction with chloroform. The organic layer was washed with a saturated saline solution and dried with anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was purified through silica gel column chromatography (chloroform/methanol), thereby obtaining the subject compound (1.16 g) as a yellow oily substance.

Workup

  1. temperaturecooling
  2. stirringstirred at room temperature for additional 30 minutes
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. additionThe residue was added with water
  5. extractionthe whole was subjected to extraction with chloroform
  6. washThe organic layer was washed with a saturated saline solution
  7. dry with materialdried with anhydrous sodium sulfate
  8. concentrationfollowed by concentration under reduced pressure
  9. customThe residue was purified through silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-718c807f17db4376b50bd1ca9536fe34
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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