Aluminium lithium hydride → HCID 58056219, compound

HRID 1773519Notes

Reaction equation

HRID 1773519 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9](=O)/[CH:10]=[CH:11]/[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([NH2:20])[CH:13]=1>O1CCCC1>[NH2:20][C:14]1[CH:13]=[C:12](/[CH:11]=[CH:10]/[CH2:9][OH:8])[CH:17]=[CH:16][C:15]=1[O:18][CH3:19]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 58056098HCID 58056098, compound

Product 1

HCID 58056219HCID 58056219, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium aluminum hydride (1 M in THF, 4 mL) was added at 0° C. to a solution of (E)-3-(3-amino-4-methoxy-phenyl)-acrylic acid methyl ester (400 mg) in tetrahydrofuran (10 mL) and the resulting mixture was stirred for 15 minutes. The reaction mixture was then quenched by addition of a saturated aqueous solution of ammonium chloride, the resulting mixture was filtered and the filter cake was washed with ethyl acetate. The filtrate was separated and the organic layer was dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to afford 90 mg of (E)-3-(3-amino-4-methoxy-phenyl)-prop-2-en-1-ol without further purifications.

Workup

  1. customThe reaction mixture was then quenched by addition of a saturated aqueous solution of ammonium chloride
  2. filtrationthe resulting mixture was filtered
  3. washthe filter cake was washed with ethyl acetate
  4. customThe filtrate was separated
  5. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-67522197fd374bb2a0aeac650df8159d
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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