Aluminium lithium hydride → HCID 57641249, compound

HRID 2112291Notes

Reaction equation

HRID 2112291 reaction equation
[CH2:1]([N:8]1[CH:16]=[C:15]2[C:10]([N:11]=[C:12]([CH3:30])[C:13]([C:25](OCC)=[O:26])=[C:14]2[C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=2[Cl:24])=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([N:8]1[CH:16]=[C:15]2[C:10]([N:11]=[C:12]([CH3:30])[C:13]([CH2:25][OH:26])=[C:14]2[C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=2[Cl:24])=[CH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57641323HCID 57641323, compound

Product 1

HCID 57641249HCID 57641249, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 7A (55 mg, 0.125 mmol) in THF (15 mL) was added LAH solution (0.4 mL, 1 M in THF, 0.4 mmol). The mixture was stirred at RT for 1.5 h and quenched with sat. NaHCO3 solution (1.5 mL) after which it was extracted with EtOAc (15 mL). The organic phase was dried (MgSO4) and concentrated in vacuo. The residue was chromatographed (SiO2; EtOAc) to give the desired compound (32 mg; 64%) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 2.78 (s, 3H), 4.43 and 4.52 (ABq, J=11.9 Hz, 2H), 5.28 (s, 2H), 6.55 (d, J=2.2 Hz, 1H), 7.06-7.38 (m, 2H), 7.20-7.38 (m, 6H), 7.53 (d, J=1.8 Hz, 1H). [M+H]+=397.17.

Workup

  1. customquenched with sat. NaHCO3 solution (1.5 mL) after which it
  2. extractionwas extracted with EtOAc (15 mL)
  3. dry with materialThe organic phase was dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed (SiO2; EtOAc)

Sources & evidence

ORD record
ord-4a67b7fe9503413d8b71153a06c5e11f
Source dataset
uspto-grants-2009_04
Patent number
US07521557B2

Reaction notes

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