Formaldehyde → HCID 178483212, compound

HRID 576473Notes

Reaction equation

HRID 576473 reaction equation
[CH3:1][N:2]([CH2:4][C-:5]1[CH:9]=[CH:8][CH:7]=[C:6]1[CH2:10][N:11]([CH3:13])[CH3:12])[CH3:3].[CH-:14]1[CH:18]=[CH:17][CH:16]=[CH:15]1.[Fe+2:19].C([Li])CCC.[CH2:25]=[O:26]>C(OCC)C>[OH:26][CH2:25][C-:9]1[CH:8]=[CH:7][C:6]([CH2:10][N:11]([CH3:13])[CH3:12])=[C:5]1[CH2:4][N:2]([CH3:1])[CH3:3].[CH-:14]1[CH:18]=[CH:17][CH:16]=[CH:15]1.[Fe+2:19]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 1317272661,2-Bis(dimethylaminomethyl)ferroceneHCID 178418339Butyllithium

Product 1

HCID 178483212HCID 178483212, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 1,2-bis-(dimethylaminomethyl) ferrocene (Example 9, 0.70 g, 2.32 mmol) in diethyl ether (15 cm3) under argon is added 1.2 equivalents n-butyl lithium (Aldrich, 1.75 mL, 1.6M in diethyl ether) and the mixture stirred for three hours to yield a red solution. The reaction mixture is cooled in a dry ice/acetone bath, calcined paraformaldehyde added in 2:1 excess, and the resultant mixture stirred at room temperature overnight. The mixture is quenched with water and extracted with diethyl ether. The ethereal extracts are dried over MgSO4, filtered over celite and the solvent removed in vacuo, to yield the title compound (0.7 g, 2.12 mmol, 91%) as an orange oil., which partially crystallized on cooling.

Workup

  1. customto yield a red solution
  2. temperatureThe reaction mixture is cooled in a dry ice/acetone bath
  3. additionadded in 2:1 excess
  4. customThe mixture is quenched with water
  5. extractionextracted with diethyl ether
  6. dry with materialThe ethereal extracts are dried over MgSO4
  7. filtrationfiltered over celite
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-ca7cd6f53e1f401fad86f8384dedadec
Source dataset
uspto-grants-2015_05
Patent number
US09040445B2

Reaction notes

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