ChemicalBook CAS DataBase List Tetrahydropyran-4-carbaldehyde

Tetrahydropyran-4-carbaldehyde synthesis

11synthesis methods

Product Name:Tetrahydropyran-4-carbaldehyde
CAS Number:50675-18-8
Molecular formula:C6H10O2
Molecular Weight:114.14

4295-99-2 Synthesis

4295-99-2
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50675-18-8
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$15.00/100mg

Yield:50675-18-8 80%

Reaction Conditions:

with diisobutylaluminium hydride in toluene at -5 - 25;Inert atmosphere;

Steps:

Tetrahydropyran-4-carbaldehyde (6)
[0169] Dry toluene (500 g) was charged into a dried reactor under nitrogen and tetrahydropyran-4-carbonitrile 5 (100 g, 0.90 mol) was added. The resulting solution was cooled to -5°C to 5°C and a solution of DIBAL-H in toluene (1.0M, 800 g, 1.0 mol) was added dropwise at -5°C to 5°C and the resulting reaction mxture was stirred at this temperature for 1-2 hrs. The reaction mixture was then warmed to 20-25°C and stirred at this temperature for 1-2 hrs. Subsequently the reaction mixture was cooled to -5°C - 5°C and quenched by the dropwise addition of a solution of AcOH (195 g) in toluene (180 g) at -5° - 5°C (caution: exothermic, gas release). A 25% solution of sodium tartrate tetrahydrate (1000 g) was added slowly at -5°C - 5°C (caution:exothermic, gas release). The reaction mixture was allowed to warm to 20-25°C and stirred at this temperature for 8-16 hrs. The layers were separated and the aqueous layer was extracted twice with EtOAc (900 mL each) at 20-25°C. The two EtOAc extracts were combined with the original organic phase and the combined organic phases were evaporated in vacuo to about 100-200 g to yield the product 6. The product was generally isolated in 50-80% yield.

References:

IMARA, INC.;SVENSTRUP, Niels;ZHANG, Jun;SUN, Jikui;CHEN, Yuyin;KONG, Jianshe;MA, Rujian;ZHANG, Junhua;QIN, Liang;XIAO, Huanming;SUN, Jinxu;MENG, Xiao;SUN, Fenglai;ZHU, Jingyang WO2018/218104, 2018, A1 Location in patent:Paragraph 0154; 0169

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14774-37-9 Synthesis