Aluminium lithium hydride → HCID 22458857, compound

HRID 2396490Notes

Reaction equation

HRID 2396490 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([C:10]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][N:21]4[CH2:26][CH2:25][CH2:24][CH:23]([CH3:27])[CH2:22]4)=[CH:14][CH:13]=3)=[O:11])=[C:8]([C:28]3[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=3)[S:7][C:6]=2[CH:35]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([CH:10]([C:12]3[CH:13]=[CH:14][C:15]([O:18][CH2:19][CH2:20][N:21]4[CH2:26][CH2:25][CH2:24][CH:23]([CH3:27])[CH2:22]4)=[CH:16][CH:17]=3)[OH:11])=[C:8]([C:28]3[CH:29]=[CH:30][C:31]([OH:34])=[CH:32][CH:33]=3)[S:7][C:6]=2[CH:35]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22458862HCID 22458862, compound

Product 1

HCID 22458857HCID 22458857, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of [6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thien-3-yl][4-[2-(3-methyl-1-piperidinyl]ethoxy]phenyl]methanone, as described in United Kingdom Patent Application GB 2097 788 H (0.300 g, 0.633 mmol), was stirred in THF (40 mL) at ambient temperature. Lithium aluminum hydride (0.100 g, 2.64 mmol) was added gradually over a 15 minute period and the reaction mixture was stirred at ambient temperature for 1.75 hours. Subsequently, the reaction was quenched with cold ethyl acetate. The mixture was evaporated and then taken up in methanol (10 mL) an ethyl acetate (30 mL). The organic layers were washed with sodium bicarbonate (25 mL of a saturated aqueous solution), potassium sodium tartrate (3×20 mL, saturated aqueous solution), and dried (magnesium sulfate). Concentration gave 0.290 g (96%) of the title compound which was used without further purification:

Workup

  1. customSubsequently, the reaction was quenched with cold ethyl acetate
  2. customThe mixture was evaporated
  3. washThe organic layers were washed with sodium bicarbonate (25 mL of a saturated aqueous solution), potassium sodium tartrate (3×20 mL, saturated aqueous solution)
  4. dry with materialdried (magnesium sulfate)
  5. concentrationConcentration

Sources & evidence

ORD record
ord-bf220d74f8c241a2948fc2b08ab7da20
Source dataset
uspto-grants-1996_02
Patent number
US05492921

Reaction notes

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