Methyl chloroformate → HCID 19927079, compound
Reaction equation
C([Li])CCC.C[Si](C)(C)[C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH:11]=[NH:12].[C:18](Cl)(=[O:34])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33].C(NC(C)C)(C)C.[Li].ClC(OC)=O>C1COCC1.C(OCC)C>[CH:11](=[NH:12])[C:10]1[CH:13]=[CH:14][CH:15]=[CH:8][CH:9]=1.[C:18]([NH:12][CH2:11][C:10]#[CH:9])(=[O:34])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -70 °C
Procedure
n-butyllithium in solution in hexanes is added in a dropwise manner to a solution of 3-trimethylsilyl benzylidenamine in solution in THF. After 30 min. of stirring at -70° C., palmitoyl chloride (1 eq.) in solution in THF is added thereto. The solution is stirred at -70° C. for 30 min., and lithium diisopropylamine (1 eq.) in solution in hexanes is added in a dropwise manner. After 20 min. of stirring at -70° C., a solution of methyl chloroformate in tetrahydrofuran is added thereto. The solution is stirred at -70° C. for 20 min. and poured into diethylether. The solution is then washed with water and brine, dried over sodium sulfate, and concentrated to yield palmitoyl propargylamine benzylidenamine.
Workup
- stirringThe solution is stirred at -70° C. for 30 min.
- stirringAfter 20 min. of stirring at -70° C.
- stirringThe solution is stirred at -70° C. for 20 min.
- washThe solution is then washed with water and brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-4fb2064114784112a1ca7f212525ce31
- Source dataset
- uspto-grants-1995_07
- Patent number
- US05430169
Reaction notes
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