Water → HCID 67399383, compound

HRID 70542

Reaction equation

HRID 70542 reaction equation
C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[I-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)[CH2:19][CH:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)C=CC=CC=1.[Cl:38][C:39]1[CH:40]=[CH:41][C:42]([CH:47]=O)=[N:43][C:44]=1[O:45][CH3:46].O>O1CCCC1>[Cl:38][C:39]1[C:44]([O:45][CH3:46])=[N:43][C:42](/[CH:47]=[CH:19]\[CH:20]2[CH2:21][CH2:22][O:23][CH2:24][CH2:25]2)=[CH:41][CH:40]=1

Participants

6

Reactant 4

HCID 962WaterHCID 2733832Lithium HexamethyldisilazideHCID 21094223Triphenyl[(tetrahydro-2H-pyran-4-yl)methyl]phosphonium iodideHCID 584528465-Chloro-6-methoxypicolinaldehyde

Product 1

HCID 67399383HCID 67399383, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of lithium hexamethyldisilazide in tetrahydrofuran (1 M, 10 mL) was added to a solution of triphenyl(tetrahydro-2H-pyran-4-ylmethyl)phosphonium iodide (5.51 g) in tetrahydrofuran (20 mL) under ice-cooling, and the mixture was stirred at room temperature for one hour. A solution of 5-chloro-6-methoxypyridine-2-carbaldehyde (1.3 g) in tetrahydrofuran (20 mL) was slowly added to the reaction solution, and the mixture was stirred at room temperature for one hour. The reaction solution was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The filtrate was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to give 3-chloro-2-methoxy-6-[(Z)-2-(tetrahydro-2H-pyran-4-yl)ethenyl]pyridine as a colorless powder (1.62 g, 60%).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for one hour
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customThe solvent was then evaporated under reduced pressure
  8. customThe filtrate was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-5cc8e5298ab243bfb54577433be3f815
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Linked notes

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