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Excepted Quantity | USD 0.00 |
Limited Quantity | USD 15-60 |
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CAS No. : | 56219-04-6 | MDL No. : | MFCD00010126 |
Formula : | C16H30O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | QFPVVMKZTVQDTL-FPLPWBNLSA-N |
M.W : | 238.41 | Pubchem ID : | 5364643 |
Synonyms : |
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Signal Word: | Danger | Class: | 9 |
Precautionary Statements: | P501-P273-P260-P270-P264-P280-P391-P314-P337+P313-P305+P351+P338-P301+P312+P330 | UN#: | 3077 |
Hazard Statements: | H302-H319-H372-H410 | Packing Group: | Ⅲ |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 92 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / 0 °C 2: 66.64 percent / pyridinium chlorochromate / CH2Cl2 / 3 h / 20 °C | ||
Multi-step reaction with 2 steps 1: 96 percent / LAH / tetrahydrofuran / 5 h / -10 - 20 °C 2: 84 percent / pyridinium chlorochromate / CH2Cl2 / 1 h / Ambient temperature | ||
With 1-methyl-piperazine; sodium bis(2-methoxyethoxy)aluminium dihydride In toluene at 20℃; for 2h; Sealed tube; Inert atmosphere; Cooling with ice; | 3 Reduction of methyl hexadec-9-enoate with sodiumbis(2-methoxyethoxy) aluminumhydride In an oven-dried, nitrogen-flushed flask sealed with a rubber septum and containing a magnetic stir bar is added 0.47 g N-methylpiperazine (CAS 109-01-3) and 10 mL of dry, degassed toluene. The flask is submerged in an ice bath and, with magnetic stirring, 1.48 g of a 70% solution of sodium bis(2-methoxyethoxy)aluminumhydride (CAS 22722-98-1) in toluene is added dropwise. In a separate oven dried, nitrogen-flushed flask sealed with a rubber septum is added 1.00 g of methyl hexadec-9-enoate, prepared through the process detailed in Example 2, and 20 mL of dry, degassed toluene. The flask is then submerged in an ice bath and stirrer via an external magnetic stirrer. After stirring for one hour, the N-methylpiperazine/sodium bis(2-methoxyethoxy)aluminumhydride mixture is added dropwise via a cannula to the toluene solution of ester. The resulting mixture is stirred at ice-bath temperature for one hour and then brought to ambient temperature and stirred for an additional hour. The reaction is quenched by addition of 20 mL of deionized water and then extracted with 20 mL of EtOAc. The organic layer is washed with 20 mL of deionized water, dried over sodium sulfated and then concentrated in vacuo. The product is analyzed by GC-MS, indicating that (Z)-hexadec-9-enal is formed in high yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In tetrahydrofuran; water; tert-butyl alcohol; at 20℃; | A solution of NaClO2 (9.26 g, 102 mmol, 7 equiv) and NaH2PO4·H2O (18.12 g, 132mmol, 9 equiv) in H2O (120 mL) was added dropwise into a mixture of aldehyde S6(3.48 g, 14.6 mmol, 1 equiv) and 2-methyl-2-butene (60 mL) in t-BuOH/THF (359 mLand 298 mL, respectively). The resulting mixture was stirred at rt until the reactionwas completed. The reaction was quenched with brine and extracted with DCM. The organic phase was washed with brine (3 × 150 mL), dried with MgSO4, andconcentrated in vacuo to afford the crude product. Flash column chromatography(pentane/ethyl acetate (10:1)) gave the pure title compound S7 as clear colorless oil(3.53 g, 13.9 mmol, 95%). |