Aluminium lithium hydride → HCID 70022689, compound

HRID 989613Notes

Reaction equation

HRID 989613 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]1[CH2:16][O:15][CH:14]2[CH:9]([C@:10]3([CH2:28][CH2:27][C@H:26]4[C:17](=[CH:18][CH2:19][C:20]5[CH2:21][C:22](=[O:29])[CH2:23][CH2:24][C:25]=54)[C@@H:12]3[CH2:13]2)[CH3:11])[O:8]1>C(OCC)C>[CH2:7]1[CH2:16][O:15][CH:14]2[CH:9]([C@:10]3([CH2:28][CH2:27][C@H:26]4[C:17](=[CH:18][CH2:19][C:20]5[CH2:21][CH:22]([OH:29])[CH2:23][CH2:24][C:25]=54)[C@@H:12]3[CH2:13]2)[CH3:11])[O:8]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 70022904HCID 70022904, compound

Product 1

HCID 70022689HCID 70022689, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a well-stirred suspension of lithium aluminum hydride (0.3 g, 7.9 mmol) in diethyl ether (20 mL) at 0° C. under nitrogen was added a solution of the ketone 3 (0.47 g, 1.52 mmol) in ether (20 mL). After stirring for 1.5 h the reaction mixture was quenched by the sequential addition of water (0.3 mL), 15% aqueous sodium hydroxide (0.3 mL) and water (1 mL) and stirred for 30 min. The inorganic precipitate was filtered out and washed with ether (3×10 mL). The ether extracts and washings were combined and concentrated to afford a mixture (4:1) of the 3α-and 3β-alcohols 4 as a foam (0.47 g, quant).

Workup

  1. customwas quenched by the sequential addition of water (0.3 mL), 15% aqueous sodium hydroxide (0.3 mL) and water (1 mL)
  2. stirringstirred for 30 min
  3. filtrationThe inorganic precipitate was filtered out
  4. washwashed with ether (3×10 mL)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8a0e95f7347e4c7b9f2a11180161266e
Source dataset
uspto-grants-2002_10
Patent number
US06458778B1

Reaction notes

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