Hydrochloric Acid → [6-(2-Fluoro-4-trifluoromethyl-phenyl)-2-methyl-pyridin-3-yl]-methanol

HRID 33544Notes

Reaction equation

HRID 33544 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9](=O)[C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][C:17]=2[F:26])=[N:12][C:11]=1[CH3:27].Cl>O1CCCC1.[Cl-].[Na+].O>[F:26][C:17]1[CH:18]=[C:19]([C:22]([F:25])([F:24])[F:23])[CH:20]=[CH:21][C:16]=1[C:13]1[N:12]=[C:11]([CH3:27])[C:10]([CH2:9][OH:8])=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 692756966-(2-Fluoro-4-trifluoromethyl-phenyl)-2-methyl-nicotinic acid methyl ester

Product 1

HCID 69106424[6-(2-Fluoro-4-trifluoromethyl-phenyl)-2-methyl-pyridin-3-yl]-methanol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

2.60 mg (68.44 mmol) lithium aluminium hydride were given to 110 ml tetrahydrofuran (THF) and stirred at room temperature (r. t.) for 20 min. A solution of 11.20 g (34.22 mmol) 6-(2-Fluoro-4-trifluoromethyl-phenyl)-2-methyl-nicotinic acid methyl ester in 110 ml THF was added drop by drop at 0° C. within 15 min., and the mixture stirred for 2 h at 0° C. 140 ml brine were added slowly at 0° C. and stirred continued for 1 h. The mixture was adjusted to pH=5 by slowly 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) and evaporated. The obtained material (9.69 g, 99%) used without further purification.

Workup

  1. stirringthe mixture stirred for 2 h at 0° C
  2. stirringstirred
  3. waitcontinued for 1 h
  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 (9.69 g, 99%) used without further purification

Sources & evidence

ORD record
ord-9d99c6b2a20f4d5286d9b27581495817
Source dataset
uspto-grants-2008_09
Patent number
US07429605B2

Reaction notes

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