Hydrochloric Acid → HCID 86634969, compound

HRID 1665218Notes

Reaction equation

HRID 1665218 reaction equation
[OH:1][N:2]=[CH:3]/[C:4](/[CH3:18])=[CH:5]/[C@@H:6]1[C@@H:8]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C:7]1([CH3:17])[CH3:16].Cl[CH2:20][C:21]#[CH:22].[H-].[Na+].Cl>CN(C=O)C>[CH3:16][C:7]1([CH3:17])[C@H:6](/[CH:5]=[C:4](\[CH3:18])/[CH:3]=[N:2][O:1][CH2:22][C:21]#[CH:20])[C@H:8]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 122213-Chloro-1-propyneHCID 24758Sodium hydrideHCID 86634965HCID 86634965, compound

Product 1

HCID 86634969HCID 86634969, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under nitrogen atmosphere, to a mixture of 0.58 g of t-butyl (1R)-trans-3-[(E)-3-hydroxyimino-2-methyl-1-propenyl]-2,2-dimethylcyclopropanecarboxylate, 0.75 g of 3-chloropropyne and 10 ml of anhydrous DMF was added 88 mg of sodium hydride (60% dispersion in mineral oil), and the mixture was stirred at room temperature overnight. Then, 1 mol/L hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, then, filtrated, and the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.46 g of t-butyl (1R)-trans-2,2-dimethyl-3-[(E)-2-methyl-3-(2-propynyloxyimino)-1-propenyl]cyclopropanecarboxylate:

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltrated
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-516b28b825114395be96581f196a633d
Source dataset
uspto-grants-2011_10
Patent number
US08039499B2

Reaction notes

Loading…