Toluene → HCID 86709384, compound

HRID 2172214Notes

Reaction equation

HRID 2172214 reaction equation
C([O:3][C:4](=O)[C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]([F:22])([F:21])[F:20])=[CH:14][CH:13]=2)=[N:7][CH:6]=1)C.C1(C)C=CC=CC=1.[H-].C([Al+]CC(C)C)C(C)C.[OH-].[Na+]>O1CCCC1>[F:22][C:19]([F:20])([F:21])[O:18][C:15]1[CH:16]=[CH:17][C:12]([O:11][C:8]2[N:7]=[CH:6][C:5]([CH2:4][OH:3])=[CH:10][CH:9]=2)=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 21225700DiisobutylaluminumhydrideHCID 70873472HCID 70873472, compound

Product 1

HCID 86709384HCID 86709384, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

6-(4-Trifluoromethoxyphenoxy)nicotinic acid ethyl ester (7.48 g, 22.9 mmol) was dissolved in tetrahydrofuran (75 ml) and cooled to −78° C. A toluene solution (100.6 ml, 100.6 mmol) of diisobutylaluminium hydride was added thereto and the mixture was stirred at the same temperature for 1 hour. The reaction mixture was poured into a 1 N sodium hydroxide aqueous solution, followed by extraction with dichloromethane. The organic layer was washed with a saturated sodium chloride aqueous solution and dried over magnesium sulfate. The organic layer was concentrated and purified by silica gel column chromatography (hexane:ethyl acetate=100:0→0:100) to afford the title compound as a colorless oil (6.15 g, 94%).

Workup

  1. extractionfollowed by extraction with dichloromethane
  2. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationThe organic layer was concentrated
  5. custompurified by silica gel column chromatography (hexane:ethyl acetate=100:0→0:100)

Sources & evidence

ORD record
ord-c0b8da3ee5484a45802960f50aace675
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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