3-Pyridinecarboxaldehyde → 2-[(3-Pyridyl)hydroxymethyl]-6-(2-methyl-1,3-dioxolan-2-yl)naphthalene

HRID 35191Notes

Reaction equation

HRID 35191 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12]3([CH3:17])[O:16][CH2:15][CH2:14][O:13]3)[CH:8]=2)[CH:3]=1.C([Li])(C)(C)C.[N:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH:29]=[O:30])[CH:24]=1>O1CCCC1>[N:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH:29]([OH:30])[C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[CH:5][CH:6]=[C:7]([C:12]4([CH3:17])[O:16][CH2:15][CH2:14][O:13]4)[CH:8]=3)[CH:3]=2)[CH:24]=1

Participants

5

Reactant 3

HCID 103713-PyridinecarboxaldehydeHCID 136879082-(6-Bromonaphthalen-2-yl)-2-methyl-1,3-dioxolaneHCID 178418306HCID 178418306, compound

Product 1

HCID 156122412-[(3-Pyridyl)hydroxymethyl]-6-(2-methyl-1,3-dioxolan-2-yl)naphthaleneYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4.5 g of 2-bromo-6-(2-methyl-1,3-dioxolan-2-yl)naphthalene in 30 ml of tetrahydrofuran was cooled to -78° C. under nitrogen, and 14.0 ml of 2.2M t-butyl lithium added dropwise. A solution of 1.64 g of 3-pyridinecarboxaldehyde in 15 ml of tetrahydrofuran was added over a period of 10 minutes, and the temperature was allowed to rise to -20° C. during the next 30 minutes. The reaction was quenched with 30 ml of water and the mixture extracted with methylene chloride. The organic layer was dried over sodium sulfate and solvent removed under reduced pressure to give a solid that was recrystallized from methylene chloride/diethyl ether to give 3.1 g of 2-[(3-pyridyl)hydroxymethyl]-6-(2-methyl-1,3-dioxolan-2-yl)naphthalene, m.p. 154°-156° C.

Workup

  1. customto rise to -20° C. during the next 30 minutes
  2. customThe reaction was quenched with 30 ml of water
  3. extractionthe mixture extracted with methylene chloride
  4. dry with materialThe organic layer was dried over sodium sulfate and solvent
  5. customremoved under reduced pressure
  6. customto give a solid
  7. customthat was recrystallized from methylene chloride/diethyl ether

Sources & evidence

ORD record
ord-91ab7496c7d048febe8a88218f6c8816
Source dataset
uspto-grants-1988_08
Patent number
US04766127

Reaction notes

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