Sodium Hydroxide → HCID 58380954, compound

HRID 45210Notes

Reaction equation

HRID 45210 reaction equation
[C:1]([C:3]1([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[CH2:7][CH:6]=[CH:5][CH2:4]1)#[N:2].[CH2:15]([Mg]Br)[CH3:16].[BH4-].[Na+].[OH-].[Na+]>C1(C)C=CC=CC=1>[NH2:2][CH:1]([C:3]1([C:8]2[CH:9]=[CH:10][C:11]([F:14])=[CH:12][CH:13]=2)[CH2:7][CH:6]=[CH:5][CH2:4]1)[CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 58380926HCID 58380926, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 58380954HCID 58380954, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-cyano-1-(4-fluorophenyl)cyclopent-3-ene (117, 1.4 g, 7.48 mmol) was dissolved in toluene (3.5 mL) and ethyl magnesium bromide (5 mL, 15 mmol, 3M in ether) added. After stirring for 2.5 hours, the reaction mixture was added dropwise to ice cold methanol (50 mL), followed by sodium borohydride (560 mg, 15 mmol). The mixture was warmed to room temperature and stirred overnight. The white suspension was treated with sodium hydroxide solution (aq, 1M, 125 mL) and then extracted with dichloromethane/isopropanol (3/1). The organic phase was washed with brine, dried over sodium sulphate and evaporated to give 1.2 g of a yellow oil. This was taken up in dichloromethane and extracted twice with dilute hydrochloric acid (2M). The combined aqueous layers were made basic with aqueous sodium hydroxide solution (5M) and re-extracted with dichloromethane/isopropanol (3/1). Drying over sodium sulphate and evaporation gave 348 mg of the desired product Rt=2.37 min (Method 2). Detected mass: 220.1 (M+H+).

Workup

  1. stirringstirred overnight
  2. extractionextracted with dichloromethane/isopropanol (3/1)
  3. washThe organic phase was washed with brine
  4. dry with materialdried over sodium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-72da54d3d05643768fdc39af373360ef
Source dataset
uspto-grants-2013_09
Patent number
US08541449B2

Reaction notes

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