Water → HCID 131714671, compound

HRID 1905745Notes

Reaction equation

HRID 1905745 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][O:7][C:8]12[CH:22]=[CH:21][CH:20]=[CH:19][CH:9]1[CH2:10][CH:11]2[CH2:12][N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)=[N+]=[N-].[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1.CCOCC>[NH2:1][CH2:4][CH2:5][CH2:6][O:7][C:8]12[CH:22]=[CH:21][CH:20]=[CH:19][CH:9]1[CH2:10][CH:11]2[CH2:12][N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 131714670HCID 131714670, compound

Product 1

HCID 131714671HCID 131714671, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of the azido benzocyclobutenylmethyl compound (0.8 g) (step 8 above) in THF (5.2 ml) is added over a period of 30 min to a suspension of LAH (0.125 g) in anhydrous ether (16.5 ml) stirred under nitrogen. The mixture is refluxed for about 2 hours and cooled. Water (0.125 ml), aqueous NaOH (15% solution, 0.125 ml) and water (3.75 ml) are added to the cooled mixture which is filtered. The solid is washed with ether and the filtrate dried over Na2SO4. The dried filtrate is filtered, evaporated in vacuo and chromatographed (silica gel) eluting with 1:1 ethyl acetate/MeOH. The pure fractions are combined and evaporated in vacuo yielding an oil. NMR analysis identifies the oil as the desired product.

Workup

  1. temperatureThe mixture is refluxed for about 2 hours
  2. temperaturecooled
  3. filtrationis filtered
  4. washThe solid is washed with ether
  5. dry with materialthe filtrate dried over Na2SO4
  6. filtrationThe dried filtrate is filtered
  7. customevaporated in vacuo
  8. customchromatographed (silica gel)
  9. washeluting with 1:1 ethyl acetate/MeOH
  10. customevaporated in vacuo
  11. customyielding an oil

Sources & evidence

ORD record
ord-41a3a1af69164375991f7fdcfd832186
Source dataset
uspto-grants-1987_03
Patent number
US04647559

Reaction notes

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