Water → HCID 69080912, compound

HRID 594223Notes

Reaction equation

HRID 594223 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl:7][C:8]1[CH:9]=[C:10]([CH:15]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[CH:17]=1)[C:11](OC)=[O:12].O.[OH-].[Na+]>C1COCC1>[Cl:7][C:8]1[CH:9]=[C:10]([CH2:11][OH:12])[CH:15]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[CH:17]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 69085397HCID 69085397, compound

Product 1

HCID 69080912HCID 69080912, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

A cooled (−10° C.) suspension of LiAlH4 (50 mg; 1.34 mmol) in anh. THF (2 ml) was treated with a solution of methyl 3-chloro-5-(pyridin-2-yl)benzoate (302 mg; 1.21 mmol) in anh. THF (1 ml). The mixture was further stirred at −10° C. for 20 min. Water (50 μl), 15% aq. NaOH (50 μl), and water (0.15 ml) were then successively added, and the resulting mixture was further stirred at rt for 1 h. Filtration, concentration to dryness under reduced pressure, and additional drying under HV afforded (3-chloro-5-(pyridin-2-yl)phenyl)methanol as a yellow oil. LC-MS (conditions A): tR=0.48 min.; [M+H]+: 220.08 g/mol.

Workup

  1. temperatureA cooled
  2. stirringthe resulting mixture was further stirred at rt for 1 h
  3. filtrationFiltration, concentration to dryness under reduced pressure
  4. customadditional drying under HV

Sources & evidence

ORD record
ord-33681ee88a2d4697bf68ecd924c1e254
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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