Aluminium lithium hydride → HCID 23288917, compound

HRID 1417799Notes

Reaction equation

HRID 1417799 reaction equation
[CH:1]1([CH2:11][CH2:12][C:13](O)=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][O:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH:1]1([CH2:11][CH2:12][CH2:13][OH:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][O:2]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 23288809170856-61-8

Product 1

HCID 23288917HCID 23288917, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 3-(isochroman-1-yl)propionic acid (LXXXVII, 0.5054 g, 2.45 mmol) in THF (2.8 ml) is added to an ice-cooled slurry of lithium aluminum hydride (0.1021 g, 2.69 mmol) in THF (3 ml). After the mixture had stirred for 30 min at 0°, it is quenched slowly with water (0.10 ml) water and allowed to stir for 15 min. An aqueous sodium hydroxide solution (15%, 0.10ml) is added and again the reaction stirred 15 min. After a final addition of water (0.3 ml) the solids are removed by filtration and washed with ether. The filtrate is washed with saline, dried over magnesium sulfate and concentrated to dryness. The crude product is chromatographed on silica gel eluting with methanol/dichloromethane (2/98). The appropriate fractions are pooled and concentrated to give 3-(isochroman-1-yl)propanol (LXXXVIII), NMR (CDCl3) 1.73, 1.92, 2.11, 2.34, 2.68, 3.03, 3.66, 3.78, 4.17, 4.82 and 7.15 δ.

Workup

  1. customit is quenched slowly with water (0.10 ml) water
  2. stirringto stir for 15 min
  3. additionAn aqueous sodium hydroxide solution (15%, 0.10ml) is added
  4. stirringagain the reaction stirred 15 min
  5. additionAfter a final addition of water (0.3 ml) the solids
  6. customare removed by filtration
  7. washwashed with ether
  8. washThe filtrate is washed with saline
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated to dryness
  11. customThe crude product is chromatographed on silica gel eluting with methanol/dichloromethane (2/98)
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-ff27918064e04c609b339cb553da9a20
Source dataset
uspto-grants-1999_03
Patent number
US05877317

Reaction notes

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