Aluminium lithium hydride → HCID 22717500, compound

HRID 1582527Notes

Reaction equation

HRID 1582527 reaction equation
[CH2:1]([O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[N:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][Si:31]([CH3:49])([CH3:48])[CH:32](I)[CH2:33][C:34]([F:46])([F:45])[C:35]([F:44])([F:43])[C:36]([F:42])([F:41])[C:37]([F:40])([F:39])[F:38])=[CH:20][N:19]=2)=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:1]([O:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2[N:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][Si:31]([CH3:48])([CH3:49])[CH2:32][CH2:33][C:34]([F:45])([F:46])[C:35]([F:44])([F:43])[C:36]([F:41])([F:42])[C:37]([F:38])([F:39])[F:40])=[CH:20][N:19]=2)=[CH:16][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22717467HCID 22717467, compound

Product 1

HCID 22717500HCID 22717500, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of compound 51 (0.89 g, 1.06 mmol) in THF (20 ml) was added dropwise to a stirred suspension of lithium aluminiumhydride (80 mg, 2.11 mmol) in THF (20 ml) under an atmosphere of dry nitrogen. The reaction mixture was stirred at room temperature overnight, heated to reflux for 1 h, cooled, washed with water and the organic layer extracted into ethyl acetate/hexane (3 times). The combined organic extracts were washed with brine, dried (MgSO4), the solvent removed in vacuo and the residues purified by column chromatography [40 g silica gel eluted with hexane/ethyl acetate (9:1)] to yield a colorless solid, which was recrystallized from ethanol.

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 h
  3. temperaturecooled
  4. washwashed with water
  5. extractionthe organic layer extracted into ethyl acetate/hexane (3 times)
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried (MgSO4)
  8. customthe solvent removed in vacuo
  9. customthe residues purified by column chromatography [40 g silica gel eluted with hexane/ethyl acetate (9:1)]
  10. customto yield a colorless solid, which
  11. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-35b474e5c6494f2ea88d9295af5ef1d6
Source dataset
uspto-grants-2004_05
Patent number
US06737124B2

Reaction notes

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