Aluminium lithium hydride → HCID 58109252, compound

HRID 2037394Notes

Reaction equation

HRID 2037394 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([OH:13])([CH3:12])[CH2:9][C:10]#[N:11])[CH:5]=[CH:6][CH:7]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1.[OH-].[Na+]>[NH2:11][CH2:10][CH2:9][C:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)([OH:13])[CH3:12]

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 58109332HCID 58109332, compound

Product 1

HCID 58109252HCID 58109252, compoundYield 135%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 3-(3-chlorophenyl)-3-hydroxybutanenitrile (400 mg, 2.04 mmol) in dry THF (10 mL) was cooled to 0° C. LiAlH4 powder (155 mg, 2 equiv.) was added. After 5 min, the mixture was warmed to rt and stirred for 4 h. The mixture was then heated to reflux for 6 h. The mixture was diluted with 1 M aq NaOH (30 mL) and extracted with CH2Cl2 (2×100 mL). The combined CH2Cl2 extracts were washed with brine, dried over Na2SO4 and concentrated to afford crude 4-amino-2-(3-chlorophenyl)butan-2-ol (550 mg, quant) which was used without purification. LC-MS Method 1, tR=0.88 min, m/z=200, 202.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureto reflux for 6 h
  3. extractionextracted with CH2Cl2 (2×100 mL)
  4. washThe combined CH2Cl2 extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-019fa77537b04235b34224efa3cb96d8
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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