Water → HCID 86639430, compound

HRID 1690215Notes

Reaction equation

HRID 1690215 reaction equation
[F:1][C:2]([F:34])([F:33])[C:3]([C:12]1[N:17]=[C:16]([CH2:18][CH2:19][CH3:20])[C:15]([O:21][C:22]2[C:27](I)=[CH:26][N:25]=[C:24]([C:29](OC)=[O:30])[CH:23]=2)=[CH:14][CH:13]=1)([O:8][CH2:9][O:10][CH3:11])[C:4]([F:7])([F:6])[F:5].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[F:33][C:2]([F:1])([F:34])[C:3]([C:12]1[N:17]=[C:16]([CH2:18][CH2:19][CH3:20])[C:15]([O:21][C:22]2[CH:27]=[CH:26][N:25]=[C:24]([CH2:29][OH:30])[CH:23]=2)=[CH:14][CH:13]=1)([O:8][CH2:9][O:10][CH3:11])[C:4]([F:7])([F:6])[F:5]

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 86639431HCID 86639431, compound

Product 1

HCID 86639430HCID 86639430, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-(6-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-2-propylpyridin-3-yloxy)-5-iodopicolinate (500 mg, 0.823 mmol) in tetrahydrofuran (8.2 mL), lithium aluminum hydride (63 mg, 1.65 mmol) was added under ice-cold conditions, and the resultant mixture was stirred at room temperature for 1 hour. After completion of the reaction, the resultant mixture was added with water under ice-cold conditions, and stirred at room temperature for 30 minutes. Then, the reaction solution was filtered using celite and extracted with chloroform. The organic layer was washed with brine, dried over sodium sulfate, and concentrated in vacuo. The obtained residue was purified using column chromatography (hexane/acetone), and (4-(6-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-2-propylpyridin-3-yloxy) pyridin-2-yl)methanol (141 mg, yield 38%) was obtained as a yellow oil.

Workup

  1. customAfter completion of the reaction
  2. filtrationThen, the reaction solution was filtered
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe obtained residue was purified

Sources & evidence

ORD record
ord-b915be27c89b40af8d89b3bff3ffd2b7
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Reaction notes

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