Sodium Hydroxide → HCID 18791123, compound

HRID 1005349Notes

Reaction equation

HRID 1005349 reaction equation
[OH-].[Na+].[C:3]([CH2:5][CH:6]1[CH2:9][CH:8]([C:10]([O:12]C)=[O:11])[CH2:7]1)#[N:4]>CO>[C:3]([CH2:5][CH:6]1[CH2:9][CH:8]([C:10]([OH:12])=[O:11])[CH2:7]1)#[N:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18791160HCID 18791160, compound

Product 1

HCID 18791123HCID 18791123, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

An aqueous solution of sodium hydroxide (1M, 295 ml) was added dropwise over a period of 30 minutes to a stirred solution of methyl 3-cyanomethylcyclobutane carboxylate (21.0 g, 0.20 mol) in methanol (300 ml). After 3 hours, the reaction mixture was washed with hexane (2×75 ml) and the aqueous phase acidified with aqueous hydrochloric acid (2M, 150 ml) to pH5. The aqueous was extracted with ethyl acetate (2×100 ml) and the combined extracts dried, filtered and evaporated to a yellow oil (21 g). The crude product was purified by chromatography on flash silica eluting with diethyl ether to give the title compound as an oil.

Workup

  1. washthe reaction mixture was washed with hexane (2×75 ml)
  2. extractionThe aqueous was extracted with ethyl acetate (2×100 ml)
  3. customthe combined extracts dried
  4. filtrationfiltered
  5. customevaporated to a yellow oil (21 g)
  6. customThe crude product was purified by chromatography on flash silica eluting with diethyl ether

Sources & evidence

ORD record
ord-16d4e7a050544577ab745cc8337e7fc7
Source dataset
uspto-grants-2000_04
Patent number
US06054448

Reaction notes

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