Aluminium lithium hydride → HCID 21912213, compound

HRID 967994Notes

Reaction equation

HRID 967994 reaction equation
Br[C:2]1[CH:23]=[C:22]([CH3:24])[C:5]([O:6][C:7]2[C:12]([CH2:13]O)=[C:11]([NH:15][CH:16]([CH2:19][CH3:20])[CH2:17][CH3:18])[CH:10]=[C:9]([CH3:21])[N:8]=2)=[C:4]([CH3:25])[CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1.C(OCC)C.[Cl-].[Al+3].[Cl-].[Cl-]>[CH3:24][C:22]1[CH:23]=[CH:2][CH:3]=[C:4]([CH3:25])[C:5]=1[O:6][C:7]1[C:12]([CH3:13])=[C:11]([NH:15][CH:16]([CH2:19][CH3:20])[CH2:17][CH3:18])[CH:10]=[C:9]([CH3:21])[N:8]=1

Participants

6

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 69587554HCID 69587554, compound

Product 1

HCID 21912213HCID 21912213, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 6451240Aluminum(III) ChlorideSolvent

Procedure

To a solution of [2-(4-bromo-2,6-dimethyl-phenoxy)-4-(1-ethyl-propylamino)-6-methyl-pyridin-3-yl]-methanol (43 mg, 0.106 mmol) in dry THF was added 1.0M lithium aluminum hydride in diethyl ether (0.25 ml) and aluminum chloride (28 mg). The resulting mixture was stirred at room temperature overnight. The mixture was quenched with water, 2 NaOH, then water. Solid formed and filtered through celite, washed with THF, then chloroform. The filtrate was concentrated to dryness. The residue was diluted with water and ethyl acetate. The organic layer was separated, dried and concentrated to give the crude material. The title compound was isolated after silica gel chromatography. 1H NMR(CDCl3) d 69-7.1(m, 3H), 6.07(s, 1H), 3.35(d, 1H), 3.33(m, 1H), 2.14(s, 3H), 2.13(s, 3H), 2.12(s, 6H), 1.5-1.8(m, 4H), 0.97(t, 6H) ppm.

Workup

  1. customThe mixture was quenched with water, 2 NaOH
  2. customSolid formed
  3. filtrationfiltered through celite
  4. washwashed with THF
  5. concentrationThe filtrate was concentrated to dryness
  6. additionThe residue was diluted with water and ethyl acetate
  7. customThe organic layer was separated
  8. customdried
  9. concentrationconcentrated
  10. customto give the crude material

Sources & evidence

ORD record
ord-4d411d4a9e6f4e98b88e1d561a064ce7
Source dataset
uspto-grants-2005_10
Patent number
US06956047B1

Reaction notes

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