Potassium Carbonate → 1-Benzyl-3-(5-hydroxymethylfur-2-yl)indazole

HRID 1594250Notes

Reaction equation

HRID 1594250 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([C:23]2[O:24][C:25]([C:28](OCC)=[O:29])=[CH:26][CH:27]=2)=[N:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[CH2:7]([N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([C:23]2[O:24][C:25]([CH2:28][OH:29])=[CH:26][CH:27]=2)=[N:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15408136HCID 15408136, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 57121-Benzyl-3-(5-hydroxymethylfur-2-yl)indazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2.06 g (54.6 mmol) of lithium aluminum hydride were initially charged in 250 ml of absolute THF, and a solution of 18.8 g (54.6 mmol) of 1-benzyl-3-(5-ethoxycarbonyl-2-furyl)indazole in 250 ml of THF was added dropwise. After 45 min the mixture was admixed with 25% strength potassium carbonate solution and stirred at RT for 30 min and the precipitate was filtered off with suction and washed with THF. The combined organic phases were concentrated using a rotary evaporator and the residue was recrystallized from isopropanol. This gave 11.0 g (67%) of the title compound. m.p.: 113-114° C.

Workup

  1. filtrationthe precipitate was filtered off with suction
  2. washwashed with THF
  3. concentrationThe combined organic phases were concentrated
  4. customa rotary evaporator
  5. customthe residue was recrystallized from isopropanol

Sources & evidence

ORD record
ord-61e5a6f3f44e412c948097b21d25aaa9
Source dataset
uspto-grants-2007_11
Patent number
US07300950B2

Reaction notes

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