Aluminium lithium hydride → HCID 22458857, compound

HRID 2184941Notes

Reaction equation

HRID 2184941 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 sulfatel. Concentration gave 0.290 g (96%) of the title compound which was used without further purification: 1H NMR (300 MHz, MeOD-d4) δ7.50 (d, 1H, J=8 Hz), 7.34 (d, 2H, J=8 Hz), 7.28 (d, 2H, J=8 Hz), 7.16 (d, 1H, J=2 Hz), 6.83-6.90 (m, 4H), 6.68 (dd, 1H, J=8 Hz, J=2 Hz), 6.10 (s, 1H), 4.13 (t, 2H, J=6 Hz), 3.00-3.25 (m, 4H), 2.85-2.92 (m, 1H), 2.32-2.43 (m, 2H), 2.08-2.19 (m, 1H), 1.42-1.51 (m, 1H), 1.05 (d, 2H, J=6 Hz); IR (KBr) 3251, 2958, 1610, 1509, 1238 1171, 838 cm−1; MS (FD) m/z 476 (M+).

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 sulfatel
  5. concentrationConcentration

Sources & evidence

ORD record
ord-1714762bbf02465f82df9de8576ba1ea
Source dataset
uspto-grants-2002_06
Patent number
US06399634B1

Reaction notes

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