Aluminium lithium hydride → HCID 13811965, compound

HRID 433851Notes

Reaction equation

HRID 433851 reaction equation
[C:1](OCC)(=[O:18])[CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][C:13](OCC)=[O:14].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[OH:14][CH2:13][CH2:12][CH2:11][O:10][CH2:9][CH2:8][O:7][CH2:6][CH2:5][O:4][CH2:3][CH2:2][CH2:1][OH:18]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22572560HCID 22572560, compound

Product 1

HCID 13811965HCID 13811965, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Prepared exactly as described, using tetrahydrofuran as solvent. (1.7 g, 5.5 mmol 14, 50 mL distilled [CaHz] THF, 0.66 g, 16.5 mmol lithium aluminum hydride). Once addition was complete, excess LAH was quenched with ethanol, and the salts precipitated by dropwise addition of saturated sodium sulfate solution until a white precipitate formed. The solvent was removed, the precipitate washed 6×30 mL with THF and the combined organic extracts were evaporated to yield an oil. Final product is purified by silica chromatography (first with methylene chloride then with ethyl acetate and finally with acetone).

Workup

  1. customPrepared exactly
  2. additionOnce addition
  3. customexcess LAH was quenched with ethanol
  4. customthe salts precipitated by dropwise addition of saturated sodium sulfate solution until a white precipitate
  5. customformed
  6. customThe solvent was removed
  7. washthe precipitate washed 6×30 mL with THF
  8. customthe combined organic extracts were evaporated
  9. customto yield an oil
  10. customFinal product is purified by silica chromatography (first with methylene chloride

Sources & evidence

ORD record
ord-af0d619d1d054c9a823902736ca2ee19
Source dataset
uspto-grants-2003_12
Patent number
US06670194B1

Reaction notes

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