Sodium sulfate decahydrate → HCID 23111775, compound

HRID 2110837Notes

Reaction equation

HRID 2110837 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([C:10]2[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=2)[CH:13]=[O:14])=[CH:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([C:10]2[CH:11]=[C:12]([CH2:13][OH:14])[CH:15]=[CH:16][CH:17]=2)=[CH:2]1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 3358918HCID 3358918, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 23111775HCID 23111775, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution (30 mL) of 3-(1-benzothiophen-3-yl)benzaldehyde (2.1 g, 8.81 mmol) in anhydrous tetrahydrofuran was added lithium aluminum hydride (0.37 g, 9.75 mmol) under ice-cooling, and the mixture was stirred at room temperature for 2 hr. The reaction solution was ice-cooled, sodium sulfate decahydrate (3.0 g, 5.74 mmol) was added, and the mixture was stirred at room temperature for 1 hr. The precipitated insoluble material was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:5-1:3) to give the title compound (2.0 g, yield 95%) as a colorless oil. 1H NMR (CDCl3) δ: 1.72 (1H, t, J=5.8 Hz), 4.80 (2H, d, J=5.8 Hz), 7.35-7.64 (7H, m), 7.88-7.98 (2H, m).

Workup

  1. temperaturecooling
  2. temperaturecooled
  3. stirringthe mixture was stirred at room temperature for 1 hr
  4. filtrationThe precipitated insoluble material was filtered through celite
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7e41111103c5499982e51fb8ee9c9e9b
Source dataset
uspto-grants-2009_04
Patent number
US07517910B2

Reaction notes

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