Hydrochloric Acid → HCID 4118077, compound

HRID 505820Notes

Reaction equation

HRID 505820 reaction equation
[CH2:1](Br)[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3].[C:11]([CH2:13][C:14]([O:16][CH3:17])=[O:15])#[N:12].CCN(C(C)C)C(C)C.Cl>C1COCC1>[C:11]([CH:13]([CH2:1][C:2](=[O:3])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:14]([O:16][CH3:17])=[O:15])#[N:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6259Phenacyl bromideHCID 7747Methyl cyanoacetateHCID 81531Diisopropylethylamine

Product 1

HCID 4118077HCID 4118077, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution (1 M) of phenacyl bromide in THF was added dropwise to a solution (5.5 M) of methyl cyanoacetate (1.1 eq.) and DIEA (2.4 eq.) in THF at RT. The resulting solution was stirred at RT for 20 h then the mixture was filtered and the filtrate was concentrated in vacuo to obtain an oil that was treated with little portions of aqueous HCl (1 N). The organic phase was washed with brine, dried and concentrated affording the title compound (97%) as an oil that solidified when stored in the fridge.

Workup

  1. filtrationthe mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customto obtain an oil that
  4. washThe organic phase was washed with brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8b7c07cc68604adab853b2e1a6d73e60
Source dataset
uspto-grants-2010_08
Patent number
US07781431B2

Reaction notes

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