Aluminium lithium hydride → HCID 117903247, compound

HRID 1485833Notes

Reaction equation

HRID 1485833 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12](/[CH:22]=[CH:23]/[N+:24]([O-])=O)=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:22][CH2:23][NH2:24])=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 117903095HCID 117903095, compound

Product 1

HCID 117903247HCID 117903247, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Nitrostyrene 28 (400 mg, 1.1 mmol) in freshly distilled THF (2 mL) was added dropwise to a solution of LiAlH4 (87 mg, 2.2 mmol), at 0° C. under an argon atmosphere. Upon completion of the reaction (from TLC) the reaction was quenched by addition of water (45 μL), 3M NaOH (45 μL), and an additional 80 μL water, and 20 mL EtOAc. The resulting mixture was stirred at room temperature for 1 h, filtered through a plug of celite, washed with EtOAc, dried (Na2SO4) and concentrated to a crude brown mixture, which was purified by column chromatography (Silica gel, 10% MeOH in DCM) to give the desired product.

Workup

  1. customUpon completion of the reaction (from TLC) the reaction
  2. customwas quenched by addition of water (45 μL), 3M NaOH (45 μL)
  3. filtrationfiltered through a plug of celite
  4. washwashed with EtOAc
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated to a crude brown mixture, which
  7. customwas purified by column chromatography (Silica gel, 10% MeOH in DCM)

Sources & evidence

ORD record
ord-ff6389cbc6f04529b57df0b0557911ef
Source dataset
uspto-grants-2016_08
Patent number
US09422320B2

Reaction notes

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