Diethyl Ether → HCID 44217645, compound

HRID 76113Notes

Reaction equation

HRID 76113 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[C:10]([C:19](OCC2C=CC=CC=2)=[O:20])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OCC)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[C:10]([CH2:19][OH:20])=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 21226445Aluminium lithium hydrideHCID 66846925HCID 66846925, compound

Product 1

HCID 44217645HCID 44217645, compoundYield 104.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzyl 1-benzyl-5-methoxy-1H-indazole-3-carboxylate (17.7 g; 0.05 mol), diethyl ether (100 ml) and tetrahydrofuran (THF) (170 ml) stirred at room temperature was slowly added LiAlH4 (3.8 g; 0.1 mol). Once the addition was complete, the suspension was stirred at reflux for 24 hours. The reaction was stopped by destroying the excess LiAlH4 via addition of water (40 ml) and 5N NaOH (10 ml). The organic phase was separated out and the solvent was evaporated off under reduced pressure. The crude residue obtained was purified by crystallization from 95° ethanol to give 14 g of (1-benzyl-5-methoxy-1H-indazol-3-yl)methanol with a melting point of 97-98° C.

Workup

  1. additionOnce the addition
  2. temperatureat reflux for 24 hours
  3. customby destroying the excess LiAlH4
  4. additionvia addition of water (40 ml) and 5N NaOH (10 ml)
  5. customThe organic phase was separated out
  6. customthe solvent was evaporated off under reduced pressure
  7. customThe crude residue obtained
  8. customwas purified by crystallization from 95° ethanol

Sources & evidence

ORD record
ord-57b977404ba44b888fdb882aedf74dfd
Source dataset
uspto-grants-2014_09
Patent number
US08835481B2

Reaction notes

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