Lithium → HCID 70418137, compound

HRID 868272Notes

Reaction equation

HRID 868272 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]([C:17](OC)=[O:18])[CH:11]=[CH:10]2.[Li]>O1CCCC1>[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]([CH2:17][OH:18])[CH:11]=[CH:10]2

Participants

4

Reactant 2

HCID 3028194LithiumHCID 70417169HCID 70417169, compound

Product 1

HCID 70418137HCID 70418137, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

0.2 g (0.75 mmol) of methyl 6-(1-imidazolylmethyl)-2-naphthoate in 5 ml of absolute tetrahydrofuran are added dropwise to 28.5 mg (0.75 mmol) of lithium alanate in 1 ml of absolute tetrahydrofuran. The mixture is allowed to stand at room temperature overnight. Excess lithium alanate is destroyed by addition of 2N HCl. After neutralization with sodium bicarbonate, the mixture is extracted with ethyl acetate, and the ethyl acetate phase is dried and evaporated in vacuo. 0.13 g (73%) of 6-(1-imidazolylmethyl)-2-naphthylmethanol is obtained. Melting point 122°-125° C.

Workup

  1. customExcess lithium alanate is destroyed by addition of 2N HCl
  2. extractionAfter neutralization with sodium bicarbonate, the mixture is extracted with ethyl acetate
  3. dry with materialthe ethyl acetate phase is dried
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-55cc10180ed3400cbac5c6b1425ae8d1
Source dataset
uspto-grants-1988_10
Patent number
US04778817

Reaction notes

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