Methanol → (E)-(3-(5-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-3-(prop-1-enyl)pyridin-2-yloxy)phenyl)methanol

HRID 1690149Notes

Reaction equation

HRID 1690149 reaction equation
[F:1][C:2]([F:33])([F:32])[C:3]([C:12]1[CH:13]=[C:14](/[CH:29]=[CH:30]/[CH3:31])[C:15]([O:18][C:19]2[CH:20]=[C:21]([CH:26]=[CH:27][CH:28]=2)[C:22](OC)=[O:23])=[N:16][CH:17]=1)([O:8][CH2:9][O:10][CH3:11])[C:4]([F:7])([F:6])[F:5].[H-].[Al+3].[Li+].[H-].[H-].[H-].CO.O>O1CCCC1>[F:33][C:2]([F:1])([F:32])[C:3]([C:12]1[CH:13]=[C:14](/[CH:29]=[CH:30]/[CH3:31])[C:15]([O:18][C:19]2[CH:20]=[C:21]([CH2:22][OH:23])[CH:26]=[CH:27][CH:28]=2)=[N:16][CH:17]=1)([O:8][CH2:9][O:10][CH3:11])[C:4]([F:7])([F:6])[F:5]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 59201011methyl (E)-3-(5-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-3-(prop-1-enyl)pyridin-2-yloxy)benzoate

Product 1

HCID 59201010(E)-(3-(5-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-3-(prop-1-enyl)pyridin-2-yloxy)phenyl)methanolYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl (E)-3-(5-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-3-(prop-1-enyl)pyridin-2-yloxy)benzoate (81 mg, 0.168 mmol) in tetrahydrofuran (2 mL), lithium aluminum hydride (9.6 mg, 0.252 mmol) was added under ice-cold conditions, and the resultant mixture was stirred at room temperature for 3 hours. The reaction solution was added with methanol and water, filtered using celite, and extracted with ethyl acetate. The organic layer was washed with brine, dried using anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified using silica-gel column chromatography (ethyl acetate), and the title compound (72 mg, yield 94.9%) was obtained as a yellow oil.

Workup

  1. filtrationfiltered
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe obtained residue was purified

Sources & evidence

ORD record
ord-106a19d435ef47c78fe170ac40f7fb78
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Reaction notes

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