Hydrochloric Acid → HCID 68289288, compound

HRID 1618895Notes

Reaction equation

HRID 1618895 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][C:9]2[CH:10]=[N:11][C:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[CH:14][C:13]=3[F:19])[C:3]=1[C:20](=[O:22])[CH3:21].[C:23]([Mg]Cl)([CH3:26])([CH3:25])[CH3:24].Cl>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][C:9]2[CH:10]=[N:11][C:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[CH:14][C:13]=3[F:19])[C:3]=1[C:20]([OH:22])([C:23]([CH3:26])([CH3:25])[CH3:24])[CH3:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 68289249HCID 68289249, compoundHCID 178418310HCID 178418310, compound

Product 1

HCID 68289288HCID 68289288, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

After 0.15 g of 1-[2-fluoro-6-(8-fluoro-quinolin-3-yloxy)-phenyl]-ethanone was dissolved in 1.5 ml of tetrahydrofuran, and then the solution was cooled to −78° C., 0.3 ml of t-butylmagnesium chloride (2.0 M diethyl ether solution) was added dropwise. After the reaction temperature was increased to room temperature, the reaction solution was treated with dilute hydrochloric acid, and then the liquid was separated with ethyl acetate. The organic layer was concentrated and then purified by silica gel column chromatography to obtain 0.04 g of 2-[2-fluoro-6-(8-fluoro-quinolin-3-yloxy)-phenyl]-3,3-dimethylbutan-2-ol (Compound Number 30).

Workup

  1. temperatureAfter the reaction temperature was increased to room temperature
  2. customthe liquid was separated with ethyl acetate
  3. concentrationThe organic layer was concentrated
  4. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-7040ca28f40647258bb452fd7a1d853f
Source dataset
uspto-grants-2014_07
Patent number
US08772200B2

Reaction notes

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