Hydrochloric Acid → HCID 86634967, compound

HRID 1665216Notes

Reaction equation

HRID 1665216 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].I[CH2:20][CH2:21][CH3:22].[OH-].[Na+].Cl>CN(C)C=O>[CH3:16][C:7]1([CH3:17])[C@H:6](/[CH:5]=[C:4](\[CH3:18])/[CH:3]=[N:2][O:1][CH2:20][CH2:21][CH3:22])[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 14798Sodium HydroxideHCID 336431-IodopropaneHCID 86634965HCID 86634965, compound

Product 1

HCID 86634967HCID 86634967, compoundYield 82.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

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, 2.0 g of 1-iodopropane and 10 ml of anhydrous dimethylformamide (hereinafter, abbreviated as DMF) was added 0.10 g of sodium hydroxide (60% dispersion in mineral oil) and the mixture was stirred at room temperature overnight. Thereafter, 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, and 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 0.56 g of t-butyl (1R)-trans-2,2-dimethyl-3-[(E)-2-methyl-3-propoxyimino-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-e1937e9649fb48b78ca002ff220d72cf
Source dataset
uspto-grants-2011_10
Patent number
US08039499B2

Reaction notes

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