Hydrochloric Acid → [5-(4-Trifluoromethyl-phenyl)-pyridin-2-yl]-methanol

HRID 33479Notes

Reaction equation

HRID 33479 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]([F:24])([F:23])[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]([CH:21]=[O:22])=[N:19][CH:20]=2)=[CH:11][CH:10]=1.[Cl-].[Na+].Cl>O1CCCC1>[F:23][C:8]([F:7])([F:24])[C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:16]=[CH:17][C:18]([CH2:21][OH:22])=[N:19][CH:20]=2)=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 21226445Aluminium lithium hydrideHCID 219361355-(4-(Trifluoromethyl)phenyl)picolinaldehyde

Product 1

HCID 21936189[5-(4-Trifluoromethyl-phenyl)-pyridin-2-yl]-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

178 mg (4.70 mmol) lithium aluminium hydride were given to 5 ml tetrahydrofuran (THF) and stirred at room temperature (r.t.) for 20 min. A solution of 590 mg (2.35 mmol) 5-(4-trifluoromethyl-phenyl)-pyridine-2-carbaldehyde in 5 ml THF was added drop by drop within 15 min., and the mixture stirred for 3 h. 9 ml conc. sodium chloride solution was added slowly at 0° C. and stirring continued for 60 min. The mixture was adjusted to pH=5 by addition of conc. HCl. A formed salt precipitate was isolated by filtration and washed with THF. The combined THF-solutions were evaporated, the residue extracted twice with ethyl acetate, the organic phase dried (sodium sulphate), evaporated, and the obtained material (270 mg, 45%) used without further purification.

Workup

  1. stirringthe mixture stirred for 3 h
  2. stirringstirring
  3. waitcontinued for 60 min
  4. customA formed salt precipitate was isolated by filtration
  5. washwashed with THF
  6. customThe combined THF-solutions were evaporated
  7. extractionthe residue extracted twice with ethyl acetate
  8. dry with materialthe organic phase dried (sodium sulphate)
  9. customevaporated
  10. customthe obtained material (270 mg, 45%) used without further purification

Sources & evidence

ORD record
ord-e0d42b7111224569a32c10d1f64d8ef8
Source dataset
uspto-grants-2008_09
Patent number
US07429605B2

Reaction notes

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