N,N,N',N'-Tetramethylethylenediamine → HCID 15204724, compound

HRID 1769053Notes

Reaction equation

HRID 1769053 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][OH:7].[Li]CCCC.CN(C)CCN(C)C.[N:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH:30]=[O:31]>CCOCC>[OH:7][CH2:6][C:5]1[CH:8]=[CH:9][CH:10]=[C:3]([O:2][CH3:1])[C:4]=1[CH:30]([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][N:24]=1)[OH:31]

Participants

6

Reactant 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 142732-PyridinecarboxaldehydeHCID 814373-Methoxybenzyl alcoholHCID 178418339Butyllithium

Product 1

HCID 15204724HCID 15204724, compoundYield 33.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 3-methoxybenzyl alcohol (50.0 g) in ether (1.1 L) at -20° C. was added n-BuLi (76.0 mL, 10.0M hexanes) at such a rate as to maintain the internal reaction temperature below -10° C. The reaction mixture was then warmed to room temperature, stirred for 2 hours, cooled to 0° C. and tetramethylethylene diamine (42.0 g) was added. The mixture was cooled to -30° C. and then 2-pyridinecarboxaldehyde (58.0 g) was added over 5 minutes. The reaction mixture was warmed to 0° C. quenched with water (500 mL) and then cooled overnight. A precipitate formed which was collected by filtration, washed with ether, and recrystallized from ethanol to afford 30.0 g of α-[2-(hydroxymethyl)-6-methoxyphenyl]-2-pyridinemethanol (Formula XIII: R1 =R7 =H; R2 =6--OCH3).

Workup

  1. temperatureto maintain the internal reaction temperature below -10° C
  2. temperaturecooled to 0° C.
  3. temperatureThe mixture was cooled to -30° C.
  4. temperatureThe reaction mixture was warmed to 0° C.
  5. customquenched with water (500 mL)
  6. temperaturecooled overnight
  7. customA precipitate formed which
  8. filtrationwas collected by filtration
  9. washwashed with ether
  10. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-3ea7691030c544c5b734af0be3b88cbb
Source dataset
uspto-grants-1995_01
Patent number
US05380729

Reaction notes

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