Methanol → HCID 53798545, compound
Reaction equation
[CH3:1][C:2](=[CH:4][CH2:5][C:6](=[N:9][OH:10])[CH2:7][CH3:8])[CH3:3].CO.C[O-].[Na+].O1C[CH2:19][CH2:18][CH2:17]1.C(Br)C=C>>[CH3:1][C:2](=[CH:4][CH2:5][C:6](=[N:9][O:10][CH2:19][CH:18]=[CH2:17])[CH2:7][CH3:8])[CH3:3]Participants
Conditions
- Temperature
- 0 °C
Procedure
A reactor was charged with 1 mole of 2-methyl-5-hydroxyimino-2-heptene, 8 moles of methanol containing 1.2 moles of sodium methylate, and 10 moles of tetrahydrofuran (THF). The mixture was cooled to 0° C., and with stirring, 1.3 moles of allyl bromide was added dropwise over 5 minutes. The mixture was stirred at room temperature for one day. The reaction mixture was concentrated, and 40 parts of methylene chloride was added. The mixture was washed with water, and the solvent was evaporated. The residue was purified by silica gel column chromatography to give 2-methyl-5-allyloxyimino-2-heptene in a yield of 80 mole %. Identification of this compound was performed by using IR, NMR and mass spectra (the same techniques were used to identify compounds appearing hereinafter).
Workup
- stirringThe mixture was stirred at room temperature for one day
- concentrationThe reaction mixture was concentrated
- addition40 parts of methylene chloride was added
- washThe mixture was washed with water
- customthe solvent was evaporated
- customThe residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-7475892712fd458aa88cf7d94d0c1dda
- Source dataset
- uspto-grants-1990_03
- Patent number
- US04906768
Reaction notes
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