Aluminium lithium hydride → HCID 22471896, compound

HRID 1071196Notes

Reaction equation

HRID 1071196 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH:7]([C:12](O)=[O:13])[CH2:6][CH2:5]2.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH:7]([CH2:12][OH:13])[CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22177058HCID 22177058, compound

Product 1

HCID 22471896HCID 22471896, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 11.4 grams (61.7 mmol) of 6-aminochroman-2-carboxylic acid in 100 mL of THF was slowly added 6.64 g (122 mmol) of lithium aluminum hydride. The mixture was refluxed for 30 min, then quenched with ethyl acetate and 150 mL of 1 N HCl. Sufficient 12 N HCl was added to completely dissolve all of the inorganic precipitates. The aqueous phase was extracted twice with ethyl acetate, and the organic fractions combined, washed twice with brine, and concentrated in vacuo to an oil. This oil was distilled to afford 9.28 g of 6-amino-2-hydroxymethylchromane as a clear oil that crystallizes on cooling (87.6% yield).

Workup

  1. temperatureThe mixture was refluxed for 30 min
  2. customquenched with ethyl acetate and 150 mL of 1 N HCl
  3. additionSufficient 12 N HCl was added
  4. dissolutionto completely dissolve all of the inorganic precipitates
  5. extractionThe aqueous phase was extracted twice with ethyl acetate
  6. washwashed twice with brine
  7. concentrationconcentrated in vacuo to an oil
  8. distillationThis oil was distilled

Sources & evidence

ORD record
ord-f2206cfcfd3c4605975edff69b36a14d
Source dataset
uspto-grants-2005_06
Patent number
US06903227B2

Reaction notes

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