Nitrogen → HCID 59133005, compound

Temperature

0 °C

A 2 L three-necked flask equipped with thermometer, stirrer, liquid sealing, N2 protection and drying tube was used. 285.4 g of MTC and 400 ml of THF were added. The flask was placed into a tank with cold bath at −15° C., to obtain a white suspension. The temperature was controlled to be between −5° C. and −10° C., and a solution of 93.3 g of t-BUOK in 400 ml of THF was added dropwise. The colour was changed into bright orange firstly, and then changed gradually into dark. After the completion of addition by dropwise, the reaction was conducted for 0.5 hour. A solution of 100 g of 4-keto-cyclohexyl formic acid methyl ester in 100 ml of THF was added dropwise at a temperature of between −5° C. and −10° C., with the colour faded gradually. After the completion of addition, the cooling was shut off, the temperature was raised naturally to about 0° C. and the reaction was conducted for 1 hour under thermal retardation. A 200 ml aqueous solution of 10 g NH4Cl was added, and the temperature was controlled to be less than 10° C. 500 ml of CH2Cl2 was added for extraction. If there is undissolved substance, a small amount of water was added to dissolve it, and washed with water till neutrality. The organic phase was tan in color, dried with anhydrous Na2SO4, and the solvent was removed by a rotary evaporator, so as to obtain a liquid-solid mixture. 500 ml of n-hexane was added, pumping filtrated, and leached with 100 ml of n-hexane twice. The filtrate was passed through a silicagel column, and the solvent was removed by a rotary evaporator, to obtain 113.5 g of pale yellow liquid. Yield: 96%, GC purity: 95.9%.

1. customdrying tube
2. addition285.4 g of MTC and 400 ml of THF were added
3. customThe flask was placed into a tank with cold bath at −15° C.
4. customto obtain a white suspension
5. customto be between −5° C. and −10° C.
6. additionAfter the completion of addition by dropwise, the reaction
7. additionAfter the completion of addition
8. waitthe reaction was conducted for 1 hour under thermal retardation
9. customto be less than 10° C
10. dissolutionto dissolve it
11. washwashed with water till neutrality
12. dry with materialdried with anhydrous Na2SO4
13. customthe solvent was removed by a rotary evaporator
14. customso as to obtain a liquid-solid mixture
15. filtrationpumping filtrated
16. customthe solvent was removed by a rotary evaporator

ORD record

ord-a762ceeaba6245a2831d131ccf7554e8

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08398887B2