Water → (1-Tritylindazol-3-yl)methanol

HRID 76115Notes

Reaction equation

HRID 76115 reaction equation
[C:1]([N:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]([C:29](OCC(C)C)=[O:30])=[N:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[C:1]([N:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]([CH2:29][OH:30])=[N:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 66846309HCID 66846309, compound

Product 1

HCID 66846262(1-Tritylindazol-3-yl)methanolYield 78.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of the crude isobutyl 1-tritylindazole-3-carboxylate (180 g; 0.39 mol) in THF (1 L) stirred at room temperature was added slowly a suspension of LiAlH4 (18 g; 0.48 mol) in THF (100 ml). Once the addition was complete, the mixture was stirred at room temperature for 30 minutes, and the reaction was then stopped by cooling the mixture to 0° C. and successively adding water (40 ml), 2N NaOH (40 ml) and water (60 ml). The solid thus formed was filtered off and the solution was concentrated under reduced pressure. The crude residue obtained was purified by crystallization from a 1/1 hexane/ethyl acetate mixture. 120 g of (1-tritylindazol-3-yl)methanol were obtained.

Workup

  1. additionwas added slowly
  2. additionOnce the addition
  3. temperatureby cooling the mixture to 0° C.
  4. customThe solid thus formed
  5. filtrationwas filtered off
  6. concentrationthe solution was concentrated under reduced pressure
  7. customThe crude residue obtained
  8. customwas purified by crystallization from a 1/1 hexane/ethyl acetate mixture

Sources & evidence

ORD record
ord-b030748ee7574ed586199bcee441325b
Source dataset
uspto-grants-2014_09
Patent number
US08835481B2

Reaction notes

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