Sodium Hydroxide → HCID 57827596, compound

HRID 1842068Notes

Reaction equation

HRID 1842068 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH2:12][CH2:11][CH2:10][C:9]=1[C:13](OCC)=[O:14].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>C1COCC1.O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH2:12][CH2:11][CH2:10][C:9]=1[CH2:13][OH:14]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21226445Aluminium lithium hydrideHCID 57827634HCID 57827634, compound

Product 1

HCID 57827596HCID 57827596, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of ethyl 2-(2-fluorophenyl)cyclopent-1-enecarboxylate obtained in Preparation Example 3-(2) (7.60 g) in THF (100 mL) was added dropwise to a suspension of lithium aluminum hydride (1.34 g) in THF (300 mL) in an ice bath. The reaction solution was stirred at the same temperature for one hour. Then, water (1.35 mL), a 5 N sodium hydroxide solution (1.35 mL) and water (4.05 mL) were sequentially added dropwise in an ice bath. Anhydrous magnesium sulfate was added to the generated reaction mixture, followed by extraction with ethyl acetate. The reaction mixture was filtered through celite and the filtrate was concentrated under reduced pressure to obtain a residue. The residue was purified by silica gel column chromatography to obtain the title compound (6.50 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. filtrationThe reaction mixture was filtered through celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customto obtain a residue
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c6ae7a2a65944ccfbcf845526a936eec
Source dataset
uspto-grants-2015_02
Patent number
US08946211B2

Reaction notes

Loading…