Aluminium lithium hydride → HCID 68763017, compound

HRID 1169881Notes

Reaction equation

HRID 1169881 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([CH:17]([O:24][CH3:25])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:12]([CH:16]=1)[C:13]([NH2:15])=O>O1CCCC1>[ClH:7].[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([CH:17]([O:24][CH3:25])[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[C:12]([CH:16]=1)[CH2:13][NH2:15]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68763871HCID 68763871, compound

Product 1

HCID 68763017HCID 68763017, compoundYield 133.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of LiAlH4 (280 mg, 7.37 mmol) in dry tetrahydrofuran (20 mL) under nitrogen atmosphere, a solution of 75 (1.0 g, 3.83 mmol) in THF (10 mL) was added and the mixture was refluxed for 3 h. After cooling, the excess of LiAlH4 was destroyed with a saturated solution of sodium sulfate. The mixture was filtered on MgSO4 and the filtrate concentrated in vacuo. The residue was partitioned between water (30 mL) and CH2Cl2 (30 mL). The aqueous-phase was separated and extracted with CH2Cl2 (20 mL×2). The combined organic phases were dried over Na2SO4, filtered and concentrated. The residue was dissolved in Et2O (5 mL) and treated with HCl/Et2O. The precipitated hydrochloride salt was filtered and triturated with dry Et2O (3×2 mL), obtaining 760 mg of product (yield 70%). 1H NMR (CD3OD, 300 MHz) δ 7.50-7.33 (m, 7H), 7.15 (d, J=9 Hz, 1H), 5.22 (s, 2H), 4.13 (s, 2H). MS (m/e) (API-ES) 248 (M−Cl)+. m.p 119-121° C.

Workup

  1. temperaturethe mixture was refluxed for 3 h
  2. temperatureAfter cooling
  3. customthe excess of LiAlH4 was destroyed with a saturated solution of sodium sulfate
  4. filtrationThe mixture was filtered on MgSO4
  5. concentrationthe filtrate concentrated in vacuo
  6. customThe residue was partitioned between water (30 mL) and CH2Cl2 (30 mL)
  7. customThe aqueous-phase was separated
  8. extractionextracted with CH2Cl2 (20 mL×2)
  9. dry with materialThe combined organic phases were dried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. dissolutionThe residue was dissolved in Et2O (5 mL)
  13. additiontreated with HCl/Et2O
  14. filtrationThe precipitated hydrochloride salt was filtered
  15. customtriturated with dry Et2O (3×2 mL)

Sources & evidence

ORD record
ord-7ddf9246c720474c9620c0e01559a822
Source dataset
uspto-grants-2010_11
Patent number
US07825126B2

Reaction notes

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