Aluminium lithium hydride → HCID 14827124, compound

HRID 1586903Notes

Reaction equation

HRID 1586903 reaction equation
C([O:9][C@H:10]1[CH2:15][CH:14]=[CH:13][CH2:12][C@H:11]1[C:16](OC)=[O:17])(=O)C1C=CC=CC=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1.O.[OH-].[Na+]>[OH:17][CH2:16][C@H:11]1[CH2:12][CH:13]=[CH:14][CH2:15][C@H:10]1[OH:9]

Participants

6

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 54330669HCID 54330669, compound

Product 1

HCID 14827124HCID 14827124, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

Methyl cis-2-benzoyloxy-cyclohex-4-enecarboxylate (6, 1.1 g, 4.19 mmol) was dissolved in THF (10 ml), and the solution added to a dispersion of lithium aluminum hydride (0.35 g, 9.15 mmol) in THF (30 ml) at -78° C. The mixture was warmed to RT and stirred for 5 hours. The reaction mixture was then cooled to -15° C., and then diluted successively with water (0.35 ml), 15% NaOH (0.35 ml), and water (1.05 ml). The precipitate was removed by filtration, washed with EtOAc, and the solvent removed under vacuum. The residual oil was purified by chromatography on silica gel (EtOAc, Rf=0.28) to yield cis 2-hydroxymethylcyclohex-4-eneol (7, 419 mg, 78%) as a colorless oil.

Workup

  1. temperatureThe reaction mixture was then cooled to -15° C.
  2. customThe precipitate was removed by filtration
  3. washwashed with EtOAc
  4. customthe solvent removed under vacuum
  5. customThe residual oil was purified by chromatography on silica gel (EtOAc, Rf=0.28)

Sources & evidence

ORD record
ord-7e8d7c0429a04c69a3df46ef56e4c143
Source dataset
uspto-grants-1993_06
Patent number
US05216141

Reaction notes

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