Tetrahydrofuran → HCID 20392276, compound

HRID 1863165Notes

Reaction equation

HRID 1863165 reaction equation
[C:1]([N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[NH:8][C:7](=O)[C:6]2=[CH:16][S:17][CH:18]=[C:5]12)(=O)[CH3:2].O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O>[CH2:1]([N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[NH:8][CH2:7][C:6]2=[CH:16][S:17][CH:18]=[C:5]12)[CH3:2]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 20392270HCID 20392270, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20392276HCID 20392276, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A reaction mixture comprising 5 g. of 4-acetyl-4,9-dihydro-10H-thieno[3,4-b][1,5]benzodiazepin-10-one in 225 ml. of dried tetrahydrofuran and 6.4 g. of lithium aluminum hydride in 150 ml. of dried tetrahydrofuran under nitrogen is stirred with heating to reflux overnight. A 6.5 ml. portion of water is added cautiously with stirring and cooling followed by 6.5 ml. of 15% sodium hydroxide and 19 ml. of water. The complex is filtered and washed thoroughly with ether. The combined filtrate and washings is dried over sodium sulfate and concentrated to a dark brown viscous oil. The oil is crystallized by treatment with 50 ml. of ether:hexane (50:50). The crystalline product is dissolved in 15 ml. of 40% methylene chloride in hexane and chromatographed on an alumina column eluting with 40% methylene chloride in hexane. Fractions 2-8 (50 ml. each) are combined and concentrated giving olive green crystals. These crystals are triturated in hexane, washed with hexane and dried giving the desired product, mp. 85°-87° C.

Workup

  1. temperaturewith heating
  2. temperatureto reflux overnight
  3. temperaturecooling
  4. filtrationThe complex is filtered
  5. washwashed thoroughly with ether
  6. dry with materialThe combined filtrate and washings is dried over sodium sulfate
  7. concentrationconcentrated to a dark brown viscous oil
  8. customThe oil is crystallized by treatment with 50 ml
  9. dissolutionThe crystalline product is dissolved in 15 ml
  10. customof 40% methylene chloride in hexane and chromatographed on an alumina column
  11. washeluting with 40% methylene chloride in hexane
  12. concentrationconcentrated
  13. customgiving olive green crystals
  14. customThese crystals are triturated in hexane
  15. washwashed with hexane
  16. customdried

Sources & evidence

ORD record
ord-fc6094da691249e1b1bcb037a98c7fd1
Source dataset
uspto-grants-1979_09
Patent number
US04168269

Reaction notes

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