Water → HCID 9877565, compound

HRID 594238Notes

Reaction equation

HRID 594238 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C[O:8][C:9]([C:11]1[CH:16]=[CH:15][N:14]=[C:13]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[CH:12]=1)=O.O.[OH-].[Na+]>C1COCC1>[N:14]1[CH:15]=[CH:16][C:11]([CH2:9][OH:8])=[CH:12][C:13]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 10727356HCID 10727356, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 9877565HCID 9877565, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

A cooled (−10° C.) suspension of LiAlH4 (40 mg; 1.05 mmol) in anh. THF (3 ml) was treated with a solution of methyl[2,2′-bipyridine]-4-carboxylate (205 mg; 0.95 mmol) in anh. THF (2 ml). The mixture was further stirred at −10° C. for 5 min., and then at rt for 20 min. Water (40 μl), 15% aq. NaOH (40 μl), and water (0.12 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 [2,2′-bipyridin]-4-ylmethanol as a colorless solid. LC-MS (conditions A): tR=0.25 min.; [M+H]+: 187.14 g/mol.

Workup

  1. temperatureA cooled
  2. waitat rt for 20 min
  3. stirringthe resulting mixture was further stirred at rt for 1 h
  4. filtrationFiltration, concentration to dryness under reduced pressure
  5. customadditional drying under HV

Sources & evidence

ORD record
ord-810dd58c2c334a95ae90f5f20ab56b28
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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