Aluminium lithium hydride → HCID 57885763, compound

HRID 1819380Notes

Reaction equation

HRID 1819380 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N:10]([CH3:12])[CH3:11])[C:5]=1[Cl:13].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[Cl:13][C:5]1[C:6]([N:10]([CH3:11])[CH3:12])=[CH:7][CH:8]=[CH:9][C:4]=1[CH2:3][OH:2]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydride2×HCID 53693012HCID 53693012, compound

Product 1

HCID 57885763HCID 57885763, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2-Chloro-3-dimethylamino-benzoic acid methyl ester (0.85 g, 3.98 mmol) was placed in a round bottomed flask with tetrahydrofuran (50 mL) and cooled to 0° C. Lithium aluminum hydride (0.30 g, 7.96 mmol) was added in portions and after all the LAH was added, the reaction was allowed to warm and stir at rt for 14. The reaction was quenched by the addition of ice, then water (10 mL) was added. The organics were extracted into ethyl acetate (3×15 mL), dried (MgSO4) and concentrated down to afford (2-chloro-3-dimethylamino-phenyl)-methanol which was taken onward without further purification.

Workup

  1. temperatureto warm
  2. customThe reaction was quenched by the addition of ice
  3. additionwater (10 mL) was added
  4. extractionThe organics were extracted into ethyl acetate (3×15 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated down

Sources & evidence

ORD record
ord-5a21a8dae729425bb639ad21308d5963
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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