Potassium Hydroxide → 4,5-Bis(phenylmethoxy)-2-pyridinemethanol

HRID 1252617Notes

Reaction equation

HRID 1252617 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([CH2:13][O:14][C:15]2[C:20]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:19][N:18]=[C:17]([C:29](OCC3C=CC=CC=3)=[O:30])[CH:16]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(=O)(O)[O-].[Na+].[OH-].[K+]>CCOCC.O1CCCC1>[C:7]1([CH2:13][O:14][C:15]2[C:20]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:19][N:18]=[C:17]([CH2:29][OH:30])[CH:16]=2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 14797Potassium HydroxideHCID 516892Sodium Bicarbonate2×HCID 14182499Benzyl 4,5-bis(benzyloxy)pyridine-2-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 141825004,5-Bis(phenylmethoxy)-2-pyridinemethanol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 95 mg (25 mmol) of lithium aluminum hydride in 10 ml of ether and 10 ml of tetrahydrofuran was added 1.06 g (25 mmol) of 4,5-bis(phenylmethoxy)-2-pyridinecarboxylic acid, phenylmethyl ester in three portions at 0° C. After stirring for 20 minutes at 0° C., 0.2 ml of saturated sodium bicarbonate solution, 0.2 ml of 10% potassium hydroxide solution and additional saturated sodium bicarbonate solution were added until the inorganic precipitate flocked together. The clear organic phase was decanted and evaporated in vacuo to yield an oil which slowly crystallized. Yield: 0.6 g, melting point 96.6° C.

Workup

  1. customThe clear organic phase was decanted
  2. customevaporated in vacuo
  3. customto yield an oil which
  4. customslowly crystallized

Sources & evidence

ORD record
ord-427887eeb0314567b82be80d7a89d8e3
Source dataset
uspto-grants-1988_05
Patent number
US04743685

Reaction notes

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