N,N,N',N'-Tetramethylethylenediamine → 2-Octen-1-ol
Reaction equation
CN(CCN(C)C)C.[CH2:9]([Li])[CH2:10][CH2:11][CH3:12].[CH2:14]=[CH:15][CH:16]1[O:18][CH2:17]1>CCCCCC>[CH2:17]([OH:18])[CH:16]=[CH:15][CH2:14][CH2:9][CH2:10][CH2:11][CH3:12]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of 258 mg of TMEDA in 1 ml of hexane was cooled to 0° C., and a hexane solution of n-butyllithium (1.1 mmol) was added dropwise thereto under a nitrogen atmosphere and stirred at 0° C. To the resultant mixture, there was added dropwise 1 ml of a hexane solution of 3,4-epoxy-butene-1 (1 mol/liter). After completion of the addition, the resultant mixture was stirred at 0° C. for 1 hour and at room temperature for 30 minutes, followed by the usual work up. After removal of the solvent, the residue was distilled to give 41 mg of 2-octen-1-ol as a colorless oily product (yield, 32%). After acetylation of the thus obtained product, gas chromatographic analysis (PEG 20M, 45 m) was effected at a temperature of 130° C. The Z/E ratio was 76.8/23.2.
Workup
- additionAfter completion of the addition
- customAfter removal of the solvent
- distillationthe residue was distilled
Sources & evidence
- ORD record
- ord-ae42ce90953d44469566b1076efa84f2
- Source dataset
- uspto-grants-1991_04
- Patent number
- US05004843
Reaction notes
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