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2nd August 2016 @ 02:00

Reference:

http://malaria.ourexperiment.org/triazolopyrazine_se/8947/Synthesis_of_methyl_234difluorophenyl2tetrahydro2Hpyran2yloxyacetate_AEW_1092.html

http://malaria.ourexperiment.org/triazolopyrazine_se/11404/Synthesis_of_methyl_2phenyl2tetrahydro2Hpyran2yloxyacetate_AEW_2191.html

 

Procedure: Reaction started at 15:17 2nd Aug

methyl 2-hydroxy-2-phenylacetate(7.8 g, 46.9 mmol, 1 equiv.) and DHP (4.7 mL, 4.34g, 51.63 mmol, 1.1 equiv.) were dissolved in anhydrous CH2Cl2 (100 mL) under Argon and cooled to 0 ˚C. TsOH (1.62 g, 9.39mmol, 0.2 eq.) was added and the reaction mixture was stirred at 0 ˚C for 3 h (black solution) and then at rt. 

CH2Cl(80 mL) was added and the resulting solution was shaken with portions of ice-cold water (3 x 10 mL) and once with saturated NaHCO(10 mL). The organic phase was dried (MgSO4) and filtered, and the solvent was removed under reduced pressure.


HIRAC:

HM 5-1.docx

String:

InChI=1S/C9H10O3/c1-12-9(11)8(10)7-5-3-2-4-6-7/h2-6,8,10H,1H3

to

InChI=1S/C14H18O4/c1-16-14(15)13(11-7-3-2-4-8-11)18-12-9-5-6-10-17-12/h2-4,7-8,12-13H,5-6,9-10H2,1H3

Log


2nd  Aug

The reaction started at 3:10pm. When adding DHP,the reaction mixture gradually turned blue(The mixture didn't become warmer so that ice bath was removed),then became darker.After an hour,TLC was performed, using 33%ethyl acetate in petrolum as mobile phase.As a result, new compound was formed though the reaction hadn't gone to completion.(impurity existed in SM)

  

 

 5th Aug

The mixture was columned using 10% of ethyl acetate in hexane as fluent phase. Two fraction was collected and NMR shows they are the product and the starting material respectively.product:1.5g, starting material 5.0g. The starting material will be used as the reactant of the same reaction again.

 

NMR

HM 5-1 frac1.zip
HM 5-1 frac2.zip
HM 5-1 frac2.png
HM 5-1 frac1.png
Attached Files
HM 5-1.png
HM 5-1.docx
IMG_2233.JPG
IMG_2235.JPG
IMG_2234.JPG
HM 5-1 frac2.png
HM 5-1 frac2.zip
HM 5-1 frac1.zip
HM 5-1 frac1.png
Comments
Re: Synthesis of methyl 2-phenyl-2-((tetrahydro-2H-pyran-2-yl)oxy)acetate(HM 5-1) by Matthew Todd
2nd August 2016 @ 06:13
HIRAC approved after discussion and on assumption that product is treated as unknown/assumed toxic.