Hydrochloric Acid → HCID 20066743, compound
Reaction equation
[CH2:1]([Li])[CH2:2][CH2:3]C.C(NC(C)C)(C)C.[CH3:13][N:14]([CH3:32])[C:15](=[O:31])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].C(Br)C=C.Cl>O1CCCC1>[CH3:32][N:14]([CH3:13])[C:15](=[O:31])[CH:16]([CH2:3][CH:2]=[CH2:1])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]Participants
Procedure
To a solution of n-butyl lithium (hexane, 44 mmol) in 120 mL of anhydrous tetrahydrofuran at 0° C., under nitrogen atmosphere it was added 6.2 mL (44 mmol) of diisopropylamine. After 5 min., 10 g (35 mmol) of N,N-dimethylhexadecanamide was added dropwise and the solution was stirred for 1 h at the same temperature. To the solution 3.7 mL (44 mmol) of allyl bromide were added and the mixture was stirred at room temperature for 12 h. Afterwards the solution was poured on water and the resulting mixture was acidified with 12 N HCl, and extracted twice with ethyl acetate. The organic phase was dried over anhydrous sodium sulfate and after evaporation of the solvent it was obtained 10.94 g of an oil that was purified by column chromatography (silica gel, hexane: ethyl acetate 15%). In that way, 10.2 g of a colorless oil was obtained (85% yield).
Workup
- stirringthe mixture was stirred at room temperature for 12 h
- additionAfterwards the solution was poured on water
- extractionextracted twice with ethyl acetate
- dry with materialThe organic phase was dried over anhydrous sodium sulfate
- customafter evaporation of the solvent it
Sources & evidence
- ORD record
- ord-fd72b1ba4c804c6e8707859de78dae7c
- Source dataset
- uspto-grants-1991_03
- Patent number
- US04997843
Reaction notes
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