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

HRID 1647716Notes

Reaction equation

HRID 1647716 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 34%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 3-methoxybenzylalcohol (50.0 g, 0.36 mol) in ether (1.1 L) at -20° C. was added n-BuLi (76.0 mL, 0.756 mol) at such a rate that the internal temperature of the reaction was maintained at less than -10° C. When the addition of n-BuLl was complete, the mixture was warmed to room temperature and stirred for 2 hours. The mixture was cooled to 0° C. and tetramethylethylene diamine (42.0 g, 0.36 reel) was added. The reaction mixture was cooled to -30° C. and 2-pyridinecarboxaldehyde (58.0 g, 0.36 mol) was added over 5 minutes. The reaction was warmed to 0° C. over a 30 minute period and was then quenched with water (500 mL). The mixture was chilled for 24 hours, and the product was collected by filtration and washed with ether. The product was recrystallized from ethanol to afford 30.0 g (34%) of α-[2-(hydroxymethyl)-6-methoxyphenyl]-2-pyridinemethanol (Formula XV: R2 =6-OCH3 ; R3 =R4 =H) . The mother liquor from the recrystallization step was concentrated, diluted with ether and refrigerated for 16 hours. A solid precipitated, which was collected by filtration to afford an additional 13.1 g of the desired product for a total of 43.1 g (49%).

Workup

  1. temperaturewas maintained at less than -10° C
  2. additionWhen the addition of n-BuLl
  3. temperatureThe mixture was cooled to 0° C.
  4. temperatureThe reaction mixture was cooled to -30° C.
  5. temperatureThe reaction was warmed to 0° C. over a 30 minute period
  6. customwas then quenched with water (500 mL)
  7. temperatureThe mixture was chilled for 24 hours
  8. filtrationthe product was collected by filtration
  9. washwashed with ether
  10. customThe product was recrystallized from ethanol

Sources & evidence

ORD record
ord-efb8ef6d95e044a483e05b9b1b6ddf5a
Source dataset
uspto-grants-1995_07
Patent number
US05434159

Reaction notes

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