Diethyl Ether → [2-Methyl-4-(2-pyridylmethoxy)phenyl]methanol

HRID 632517Notes

Reaction equation

HRID 632517 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[CH:6][C:5]=1[CH3:18].[H-].C([Al+]CC(C)C)C(C)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+].C(OCC)C>C1(C)C=CC=CC=1>[CH3:18][C:5]1[CH:6]=[C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[CH:8]=[CH:9][C:4]=1[CH2:3][OH:2]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 9357Potassium Sodium TartrateHCID 21225700DiisobutylaluminumhydrideHCID 117888980HCID 117888980, compound

Product 1

HCID 117888981[2-Methyl-4-(2-pyridylmethoxy)phenyl]methanolYield 93.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To 1.0 g of 2-methyl-4-(2-pyridylmethoxy)benzoic acid methyl ester was added 8 mL of toluene under argon atmosphere. To the mixture cooled to −78° C., 8.7 mL of a solution of diisobutylaluminium hydride (1.0 mol/L) in toluene was added dropwise. The mixture was stirred at the same temperature for 6 hours and further stirred at −35° C. for 1 hour. To the reaction mixture, a saturated aqueous Rochelle salt solution was added, and the mixture was stirred at room temperature for 30 minutes. To this, 150 mL of diethyl ether was added, and the organic layer was separated. The obtained organic layer was dried over Na2SO4 and concentrated to give 0.83 g of the title compound (93% yield).

Workup

  1. stirringfurther stirred at −35° C. for 1 hour
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. customthe organic layer was separated
  4. dry with materialThe obtained organic layer was dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-23d68ca47a124717bac970bb28629911
Source dataset
uspto-grants-2016_04
Patent number
US09321752B2

Reaction notes

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