Aluminium lithium hydride → HCID 86679333, compound

HRID 529874Notes

Reaction equation

HRID 529874 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]=1[C:17]1[CH:21]=[C:20]([CH:22]=[O:23])[S:19][C:18]=1[CH:24]=[O:25]>C1COCC1>[CH:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]=1[C:17]1[CH:21]=[C:20]([CH2:22][OH:23])[S:19][C:18]=1[CH2:24][OH:25]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86679331HCID 86679331, compound

Product 1

HCID 86679333HCID 86679333, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

About 0.022 mole of lithium aluminum hydride may be stirred into about 50 milliliters of anhydrous THF to make a slurry under an inert atmosphere, and cooled in an ice bath. About 0.01 mole of 3-(naphth-2-yl)-2,5-diformylthiophene may be dissolved in about 10 milliliters of anhydrous THF and added to the slurry with stirring. The reaction may be stirred and allowed to rise to room temperature, and then refluxed for about 2 hours. The reaction mixture may be cooled, carefully quenched with about 50 milliliters of water and washed with about 0.1 M sodium hydroxide. The organic layer may be dried, and the solvent may be removed to leave a residue. The residue may be purified via silica gel chromatography to give (3-(naphthalen-2-yl)thiophene-2,5-diyl)dimethanol.

Workup

  1. temperaturecooled in an ice bath
  2. additionadded to the slurry
  3. customThe reaction
  4. stirringmay be stirred
  5. customto rise to room temperature
  6. temperaturerefluxed for about 2 hours
  7. temperatureThe reaction mixture may be cooled
  8. customcarefully quenched with about 50 milliliters of water
  9. washwashed with about 0.1 M sodium hydroxide
  10. customThe organic layer may be dried
  11. customthe solvent may be removed
  12. customto leave a residue
  13. customThe residue may be purified via silica gel chromatography

Sources & evidence

ORD record
ord-f3ea8502dba942bd8e4ac4a9279d6e9b
Source dataset
uspto-grants-2016_05
Patent number
US09350012B2

Reaction notes

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