Lithium → HCID 13687921, compound

HRID 569799Notes

Reaction equation

HRID 569799 reaction equation
[OH:1][CH:2]([C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH:16]=[C:15]([C:20](OC(C)C)=[O:21])[CH:14]=[CH:13]2)[C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[CH3:9].[Li]>O1CCCC1>[OH:21][CH2:20][C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[C:10]([CH:2]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[CH3:9])[OH:1])[CH:19]=[CH:18]2

Participants

4

Reactant 2

HCID 3028194Lithium2×HCID 13687920HCID 13687920, compound

Product 1

HCID 13687921HCID 13687921, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

0.3 g (0.9 mmol) of isopropyl 6-[1-hydroxy-1-(4-methyl-3-pyridyl)methyl]-2-napthoate in 5 ml of absolute tetrahydrofuran is added, at 0° C., to 38 mg (1 mmol) of lithium alanate in 1 ml of absolute tetrahydrofuran, and the mixture is then stirred at room temperature (24 h). After addition of a further 40 mg (1 mmol) of lithium alanate the mixture is stirred at room temperature for 24 h. Excess lithium alanate is destroyed with 2 N HCl, and the solution is neutralized with sodium bicarbonate solution. It is extracted with ethyl acetate, and this is evaporated, and the residue is chromatographed on silica gel using ethyl acetate/methanol 4:1. 0.16 g (65%) of 1-(6-hydroxymethyl-2-naphthyl)-1-(4-methyl-3-pyridyl)methanol is obtained. Melting point 151°-3° C.

Workup

  1. stirringis stirred at room temperature for 24 h
  2. customExcess lithium alanate is destroyed with 2 N HCl
  3. extractionIt is extracted with ethyl acetate
  4. customthis is evaporated
  5. customthe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-dbbdaf852a8548a7a9a09bbb754b948a
Source dataset
uspto-grants-1988_03
Patent number
US04734406

Reaction notes

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