Diethyl Ether → 3-Hydroxymethyl-2-methyl-4-(3-nitrophenyl)-6-phenylpyridine

HRID 1762158Notes

Reaction equation

HRID 1762158 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)C.[CH3:12][C:13]1[C:18]([C:19](OCC)=[O:20])=[C:17]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([N+:30]([O-:32])=[O:31])[CH:25]=2)[CH:16]=[C:15]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[N:14]=1.C(OCC)(=O)C>O1CCCC1>[OH:20][CH2:19][C:18]1[C:13]([CH3:12])=[N:14][C:15]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:16][C:17]=1[C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([N+:30]([O-:32])=[O:31])[CH:25]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8857Ethyl AcetateHCID 10248079Ethyl 2-methyl-4-(3-nitrophenyl)-6-phenyl-3-pyridinecarboxylateHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 104712403-Hydroxymethyl-2-methyl-4-(3-nitrophenyl)-6-phenylpyridineYield 30.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (0.32 g) in a mixture of dry tetrahydrofuran (4 ml) and diethyl ether (8 ml) was dropwise added a solution of ethyl 2-methyl-4-(3-nitrophenyl)-6-phenyl-3-pyridinecarboxylate (1 g) in dry tetrahydrofuran (4 ml) at -20° C. to -10° C. The excess lithium aluminum hydride was decomposed by a careful addition to ice water. Ethyl acetate (25 ml) was added thereto and the separated organic layer was washed with 10% sulfuric acid (15 ml), saturated aqueous sodium bicarbonate and aqueous sodium chloride successively and concentrated in vacuo. The residue was subjected to a column chromatography on silica gel eluting with chloroform. The fractions containing the desired compound were combined and evaporated in vacuo. The residue was crystallized from diethyl ether to give 3-hydroxymethyl-2-methyl-4-(3-nitrophenyl)-6-phenylpyridine (0.27 g).

Workup

  1. washthe separated organic layer was washed with 10% sulfuric acid (15 ml), saturated aqueous sodium bicarbonate and aqueous sodium chloride successively
  2. concentrationconcentrated in vacuo
  3. additionThe fractions containing the desired compound
  4. customevaporated in vacuo
  5. customThe residue was crystallized from diethyl ether

Sources & evidence

ORD record
ord-4fa4b0adab0744c2a5778db72b9742eb
Source dataset
uspto-grants-1989_05
Patent number
US04831030

Reaction notes

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