Tetrahydrofuran → HCID 20392227, compound

HRID 1863172Notes

Reaction equation

HRID 1863172 reaction equation
[CH2:1]([N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[NH:8][C:7]2=[CH:15][S:16][CH:17]=[C:6]2[C:5]1=O)[CH:2]=[CH2:3].O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>CCCCCC.O>[CH2:1]([N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[NH:8][C:7]2=[CH:15][S:16][CH:17]=[C:6]2[CH2:5]1)[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 20392268HCID 20392268, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20392227HCID 20392227, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8058HexaneSolvent

Procedure

A solution of 4.6 g. of 9-allyl-4,9-dihydro-10H-thieno[3,4-b][1,5]benzodiazepin-10-one in 100 ml. of dried tetrahydrofuran is added dropwise with stirring, under nitrogen, to a suspension of 2.9 g. of lithium aluminum hydride in 100 ml. of dried tetrahydrofuran. The reaction mixture is heated under reflux with stirring overnight, then cooled in an ice bath and treated, with stirring under nitrogen, with 3 ml. of water, 3 ml. of 15% sodium hydroxide and finally with 9 ml. of water. The complex is filtered and washed several times with ether. The combined filtrate and washings are dried over sodium sulfate, filtered and the filtrate is concentrated to a dark blue oil. This oil is dissolved in 20 ml. of 30% methylene chloride in hexane and chromatographed on an alumina column as described in the previous example. Concentration of the solvent mixture yields a dark green oil which is heated to boiling in 80 ml. of hexane. The boiling hexane is decanted from a dark brown insoluble oil and then cooled giving crystals of the desired product, mp. 67°-69° C.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux
  3. stirringwith stirring overnight
  4. temperaturecooled in an ice bath
  5. additiontreated
  6. stirringwith stirring under nitrogen, with 3 ml
  7. filtrationThe complex is filtered
  8. washwashed several times with ether
  9. dry with materialThe combined filtrate and washings are dried over sodium sulfate
  10. filtrationfiltered
  11. concentrationthe filtrate is concentrated to a dark blue oil
  12. dissolutionThis oil is dissolved in 20 ml
  13. customof 30% methylene chloride in hexane and chromatographed on an alumina column
  14. customConcentration of the solvent mixture yields a dark green oil which
  15. temperatureis heated
  16. customThe boiling hexane is decanted from a dark brown insoluble oil
  17. temperaturecooled

Sources & evidence

ORD record
ord-628930de492c419d930aa27d72c779b6
Source dataset
uspto-grants-1979_09
Patent number
US04168269

Reaction notes

Loading…