Water → HCID 13391718, compound

HRID 483090Notes

Reaction equation

HRID 483090 reaction equation
[CH:1]([C:4]1[C:12]([CH:13]([O:17][CH2:18][CH:19]2[O:21][CH2:20]2)[CH:14]([CH3:16])[CH3:15])=[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][N:6]2[N:5]=1)([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].O>O1CCCC1.CCOCC>[CH:1]([C:4]1[C:12]([CH:13]([O:17][CH2:18][CH:19]([OH:21])[CH3:20])[CH:14]([CH3:15])[CH3:16])=[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][N:6]2[N:5]=1)([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 20242524HCID 20242524, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 13391718HCID 13391718, compoundYield 83.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1 g of 2-isopropyl-3-[1-(2,3-epoxypropoxy)-2-methylpropyl]pyrazolo[1,5-a]pyridine (Example 34) in 10 ml of tetrahydrofuran was added to a suspension of 330 mg of lithium aluminum hydride in 10 ml of dry tetrahydrofuran under cooling. The mixture was stirred for 40 minutes, followed by addition of 1 ml of aqueous 15% sodium hydroxide solution with cooling, 3 ml of water and an adequate amount of ether successively. The resulting precipitates were filtered off and the filtrate was extracted with ether. The ether layer was dried over anhydrous sodium sulfate and concentrated to dryness. The residue was recrystallized from hexane to give 840 mg (83%) of the desired product as colorless crystals, mp 112° C.

Workup

  1. temperatureunder cooling
  2. temperaturewith cooling
  3. customThe resulting precipitates
  4. filtrationwere filtered off
  5. extractionthe filtrate was extracted with ether
  6. dry with materialThe ether layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated to dryness
  8. customThe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-8f326d179a0d4bcfb652e8ae3be63f4d
Source dataset
uspto-grants-1986_03
Patent number
US04578392

Reaction notes

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