Hydrochloric Acid → HCID 67397793, compound

HRID 70589Notes

Reaction equation

HRID 70589 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][C:27]1[CH:32]=[CH:31][C:30](/[C:33](/[C:40]2[N:45]=[C:44]([O:46][CH3:47])[C:43]([CH2:48][CH3:49])=[CH:42][CH:41]=2)=[CH:34]\[CH:35]2[CH2:39][CH2:38][CH2:37][CH2:36]2)=[CH:29][C:28]=1[Cl:50])(C(C)(C)C)(C)C.O.Cl>O1CCCC1>[Cl:50][C:28]1[CH:29]=[C:30](/[C:33](/[C:40]2[CH:41]=[CH:42][C:43]([CH2:48][CH3:49])=[C:44]([O:46][CH3:47])[N:45]=2)=[CH:34]\[CH:35]2[CH2:36][CH2:37][CH2:38][CH2:39]2)[CH:31]=[CH:32][C:27]=1[OH:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 67396209HCID 67396209, compound

Product 1

HCID 67397793HCID 67397793, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran (1.73 mL) was added to a solution of 6-[(E)-1-(4-{[tert-butyl(dimethyl)silyl]oxy}-3-chlorophenyl)-2-cyclopentylethenyl]-3-ethyl-2-methoxypyridine (409 mg) in tetrahydrofuran (3 mL) under ice-boiling, and the mixture was stirred at room temperature for two hours. The reaction solution was poured into water and made acidic with 1 M hydrochloric acid, 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 residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1→1:1) to give 2-chloro-4-[(E)-2-cyclopentyl-1-(5-ethyl-6-methoxypyridin-2-yl)ethenyl]phenol as a yellow oil (306 mg, 99%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was then evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1→1:1)

Sources & evidence

ORD record
ord-a422f13b9d264ec8996a2f55817b5603
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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